Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA This article is part of the Thematic Series "Recent developments in chemical diversity". chemical diversity cycloisomerization cyclopropane diyne isochromene π-acid Sequential cycloisomerizations of diynyl o -benzaldehyde substrates to access novel polycyclic cyclopropanes are reported. The reaction sequence involves initial Cu(I)-mediated cycloisomerization/nucleophilic addition to an isochromene followed by diastereoselective Pt(II)-catalyzed enyne cycloisomerization.

Our laboratory has an ongoing interest in discovering transformations that afford novel chemotypes . To this end, we have developed a reaction screening paradigm that enables the discovery of new reaction processes and chemotypes . For example, we have conducted multidimensional reaction screens using alkynyl o -benzaldehyde scaffolds, which revealed a number of reactions affording novel polycyclic scaffolds, including Au(III)-catalyzed addition of diethyl malonate to 1 to afford isochromene 2 ( ). The chemotypes discovered in initial pilot studies have been further developed into library scaffolds and identified as biologically interesting structures . Herein, we report the expanded utility of alkynyl o -benzaldehydes through a sequential metal-catalyzed cycloisomerization process to afford a novel polycyclic cyclopropane chemotype.

In an effort to further explore the utility of alkynyl o -benzaldehydes as scaffolds for reaction screening, we designed a focused reaction screen with diynyl benzaldehyde substrate 3 . Based on the cycloisomerization/addition reactions previously studied ( ), it was not clear at the outset of our study whether an o -alkynyl benzaldehyde containing an additional alkynyl moiety ( 3 ) would react to form an isochromene derivative or whether additional polycyclization would occur . Accordingly, a reaction screen was conducted, evaluating a number of metal catalysts in the presence of diethyl malonate. From this focused reaction screen we identified three types of reactivity: (1) no reaction; (2) alkyne hydration ( 4 ); and (3) cycloisomerization leading to isochromene ( 5 ) ( ). Many catalysts resulted in no reaction, including ones that might have been expected to catalyze cycloisomerization, such as AgOTf. Two catalysts, Cu(OTf) 2 and Pd(MeCN) 2 Cl 2 , afforded only hydration of the alkyne. Interestingly, hydration was regioselective, which is possibly due to direction from the ether oxygen. We were most interested in metal catalysts that effected cycloisomerization of 3 to alkynyl isochromene 5 , which is an interesting enyne substrate with potential for further reactivity . In the reaction screen of alkynyl benzaldehyde substrate 3 , we found that in the absence of optimization Cu(MeCN) 4 PF 6 afforded the highest isolated yield of 5 (60%) ( ). As the production of isochromene 5 offered a unique opportunity for additional cycloisomerization processes, we elected to explore this manifold of reactivity. Based on reports by Echavarren and co-workers , we treated enyne 5 with PtCl 2 at 80 °C in toluene . The reaction afforded polycyclic cyclopropane 6 in good yield (65%) as a single diastereomer ( ). Interestingly, reaction of 3 in the presence of only PtCl 2 afforded exclusively isochromene 5 in low yield. Further studies revealed that a multicatalytic reaction system utilizing both Cu(I) and Pt(II) catalysts afforded the desired cyclopropane 6 in moderate yield (40%) along with ketone 7 (45%), derived from [4 + 2] cycloaddition of the benzopyrylium intermediate with the pendent alkyne ( ). However, better yields were observed when the initial cycloisomerization was carried out in the presence of Cu(MeCN) 4 PF 6 followed by the addition of PtCl 2 to the reaction mixture ( ). Optimization of the one-pot conditions afforded exclusively 6 in good yield (89%). X-ray crystal analysis confirmed the structure and relative stereochemistry of polycyclic cyclopropane 6 ( , ). We next focused on an evaluation of the general scope of the reaction with regard to aryl and alkyne substitution. Reaction utilizing an electron-poor trifluoromethyl-substituted diynyl benzaldehyde 8 was successful, producing product 9 in moderate yield ( , entry 1). m -Methyl- and naphthyl-containing substrates 10 and 12 afforded polycyclic cyclopropanes 11 and 13 in 48 and 51% yields, respectively ( , entries 2 and 3). We next explored substitution of the pendant alkyne. Reaction with cyclohexane diyne 14 afforded the fused cyclopropane 15 in moderate yield (60%), while methyl ether 16 afforded cyclopropane 17 in 62% yield. Phenyl substitution ( 18 ) also resulted in a moderate yield (59%, , entry 6). Substituting the oxygen with N -tosyl ( 20 ) afforded N -tosyl cyclopropane 21 in good yield (82%). Substitution at the internal methylene ( 22 ) resulted in a diverted reaction pathway (vida infra) affording product 23 exclusively in moderate yield (65%). A proposed mechanistic pathway for diastereoselective, sequential cycloisomerizations is shown in . We propose the initial cycloisomerization and nucleophilic addition of diynyl benzaldehyde 3 and dimethyl malonate is catalyzed by Cu(I) to afford isochromene 24 . Pt(II) π-coordination of the pendant alkyne of 24 followed by cyclization of the enol ether affords the seven-membered-ring metal-“ate” intermediate 25 . The cyclization occurs at the face opposite the malonate substituent (Nu, 24a ) to minimize steric interactions relative to 24b , leading to the observed diastereoselectivity ( , inset) . Subsequent cyclopropane formation through addition of the vinyl metal to the oxonium intermediate affords metallocarbenoid 26 , which may then undergo a 1,2-hydride shift to intermediate 27 followed by elimination of the metal catalyst to afford the observed cyclopropane product 6 . An alternative reaction pathway may be invoked for the ethyl-substituted substrate 22 leading to product 23 ( ). After initial cyclization of the enol ether with the Pt-activated alkyne, the resulting metal-“ate” intermediate 28 may undergo preferential elimination and proto-demetallation to afford 1,5-diene 29 . A second elimination results in the ring-opened triene 30 . Subsequent 6π-electrocyclization affords alcohol 31 , which aromatizes through loss of water to afford the observed isochromane 23 .

We have described sequential cycloisomerizations of diynyl o -benzaldehyde substrates to access novel polycyclic cyclopropanes. The reaction sequence involves initial Cu(I)-mediated cycloisomerization/nucleophilic addition to an isochromene followed by diastereoselective Pt(II)-catalyzed enyne cycloisomerization. The chemistry reported herein illustrates the power of sequential cycloisomerization processes to provide access to novel chemotypes and chemical diversity from readily accessible building blocks . Further transformations of the novel polycyclic cyclopropanes as well as additional studies employing reaction screening for metal-mediated processes is ongoing and will be reported in future publications.

General Information: All nuclear magnetic resonance spectra were recorded on either a Varian or Bruker spectrometer. 1 H NMR spectra were recorded at 400 MHz at ambient temperature with CDCl 3 as solvent, unless otherwise stated. 13 C NMR spectra were recorded at 100.0 MHz at ambient temperature with CDCl 3 as solvent, unless otherwise stated. Chemical shifts are reported in parts per million relative to CDCl 3 ( 1 H, δ 7.27; 13 C, δ 77.0) and acetone- d 6 ( 1 H, δ 2.05; 13 C, δ 30.8). Data for 1 H NMR are reported as follows: chemical shift, multiplicity (ovrlp = overlapping, s = singlet, d = doublet, t = triplet, q = quartet, qt = quintuplet, m = multiplet), coupling constant in hertz, and integration. All 13 C NMR spectra were recorded with complete proton decoupling. Analytical LC was performed on a 2.1 × 50 mm, 1.7 μM C18 column. Analytical thin-layer chromatography was performed by using 0.25 mm silica gel 60-F plates. Otherwise, flash chromatography was performed by using 200–400 mesh silica gel. Yields refer to chromatographically and spectroscopically pure materials, unless otherwise stated. Acetonitrile, CH 2 Cl 2 , THF, and toluene were purified by passing through two packed columns of neutral alumina. All reactions were performed under an argon atmosphere in oven-dried or flame-dried glassware. General procedure for the synthesis of alkynyl o -benzaldehydes: 2-(3-(but-2-ynyloxy)prop-1-ynyl)benzaldehyde. To a solution of 2-bromobenzaldehyde (2.0 g, 10.8 mmol) and 1-(prop-2-ynyloxy)but-2-yne (1.4 g, 13 mmol) in Et 3 N (68 mL), was added tetrakis(triphenylphosphine)palladium(0) (0.38 g, 0.32 mmol). The reaction mixture was stirred at room temperature for 5 min. Copper(I) iodide (0.075 g, 0.4 mmol) was added, and the mixture was heated to 60 °C overnight. The mixture was concentrated in vacuo and purified by flash chromatography (SiO 2 , petroleum ether/EtOAc 4:1) to afford diynyl benzaldehyde 3 (1.5 g, 7.1 mmol, 66%) as a viscous yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ 10.22 (s, 1H), 7.91 (d, J = 7.6 Hz, 1H), 7.57 (m, 2H), 7.46 (m, 1H), 4.54 (s, 2H), 4.29 (q, J = 2.4 Hz, 2H), 1.89 (t, J = 2.4 Hz, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 191.6, 136.2, 133.8, 133.6, 129.0, 127.3, 126.1, 91.9, 83.7, 82.2, 74.2, 57.6, 57.1, 3.7; IR (thin film) ν max : 2920, 2852, 1697, 1594, 1477, 1450, 1350, 1274, 1244, 1193, 1138, 1076, 765 cm −1 . General one-pot procedure for sequential cycloisomerization: To a flame-dried round-bottom flask was added 3 (10 mg, 0.046 mmol), dimethyl malonate (5.8 μL, 0.05 mmol) and toluene (1.0 mL). To the reaction mixture was added tetrakis(acetonitrile)copper(I) hexafluorophosphate (1.7 mg, 0.005 mmol), and the reaction mixture was stirred at room temperature for 1 h. Platinum(II) chloride (1.2 mg, 0.005 mmol) was added and the reaction mixture was heated to 80 °C for 5 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (SiO 2 , petroleum ether/EtOAc 9:1 to 4:1) to afford the desired cycloisomerization product 6 (14 mg, 0.041 mmol, 89%) as a white solid. 1 H NMR (400 MHz, CDCl 3 ) δ 7.25 (m, 2H), 7.08 (m, 1H), 6.98 (d, J = 4.2 Hz, 1H), 6.11 (d, J = 5.6 Hz, 1H), 5.28 (d, J = 10.4 Hz, 1H), 5.07 (d, J = 5.6 Hz, 1H), 4.33 (d, J = 10.0 Hz, 1H), 3.92 (d, J = 10.8 Hz, 1H), 3.83 (s, 3H), 3.66 (d, J = 10.0 Hz, 1H), 3.49 (s, 3H), 2.51 (s, 1H), 0.73 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 167.3, 166.4, 141.0, 135.8, 133.7, 130.8, 130.3, 128.9, 126.2, 111.1, 75.0, 63.9, 62.7, 59.4, 53.2, 52.7, 30.5, 26.4, 12.2; IR (thin film) ν max : 2953, 2926, 2870, 1761, 1741, 1679, 1639, 1493, 1435, 1341, 1253, 1194, 1144, 1073, 1018, 912, 774, 749 cm −1 ; HRMS–ESI + ( m / z ): [M + Na] + calcd for C 19 H 20 O 6 , 367.1158; found, 367.1189.

Reaction screen with diynyl benzaldehyde 3 .

X-ray crystal structure of cyclopropane 6 .

Cycloisomerization/nucleophilic addition of alkynyl benzaldehyde 1 to isochromene 2 . Sequential cycloisomerizations of substrate 3 . Condition A: PtCl 2 (10 mol %), Cu(MeCN) 4 PF 6 (10 mol %), toluene, 80 °C, 8 h (40%). Condition B: Step 1: Cu(MeCN) 4 PF 6 (10 mol %), rt, 1 h. Step 2: PtCl 2 (10 mol %), 80 °C, toluene, 5 h (89%). Proposed reaction pathway for diastereoselective, sequential cycloisomerization. Proposed alternative reaction pathway affording 23 . entry aldehyde product yield entry aldehyde product yield 1 8 9 53% 5 16 17 62% 2 10 11 48% 6 18 19 59% 3 12 13 51% 7 20 21 82% 4 14 15 60% 8 22 23 65%

Sequential cycloisomerizations of diynyl benzaldehyde substrates.

BEPAFCGSDWSTEL-UHFFFAOYSA-N InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3 COC(=O)CC(=O)OC C(CC(OC)=O)(OC)=O |(86.73,-37.55,;96.69,-31.8,;106.66,-37.55,;116.63,-31.8,;116.63,-20.3,;106.66,-49.06,;76.76,-31.8,;66.8,-37.55,;86.73,-49.06,)| AuxInfo=1/0/N:5,7,2,1,3,8,9,4,6/E:(1,2)(4,5)(6,7)(8,9)/rA:9nCCCOCOCOO/rB:s1;s2;s1;s4;s3;s6;d1;d3;/rC:86,7274,-37,5516,0;96,6942,-31,7973,0;106,6610,-37,5516,0;76,7606,-31,7973,0;66,8013,-37,5473,0;116,6278,-31,7973,0;116,6278,-20,2973,0;86,7274,-49,0603,0;106,6610,-49,0603,0; C5H8O4 CO* OMe CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 9 8 0 0 0 M V30 BEGIN ATOM M V30 1 C 86.72743 -37.55164 0 0 M V30 2 C 96.69421 -31.7973 0 0 M V30 3 C 106.661 -37.55164 0 0 M V30 4 O 76.76064 -31.7973 0 0 M V30 5 C 66.80135 -37.54729 0 0 M V30 6 O 116.62779 -31.7973 0 0 M V30 7 C 116.62778 -20.2973 0 0 M V30 8 O 86.72743 -49.06029 0 0 M V30 9 O 106.661 -49.06029 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 1 2 M V30 2 1 2 3 M V30 3 1 4 5 M V30 4 1 1 4 M V30 5 1 6 7 M V30 6 1 3 6 M V30 7 2 1 8 M V30 8 2 3 9 M V30 END BOND M V30 END CTAB M END PFSIMRPMFLXAIS-UHFFFAOYSA-N InChI=1S/C19H20O6/c1-4-5-10-24-12-14-11-13-8-6-7-9-15(13)17(25-14)16(18(20)22-2)19(21)23-3/h6-9,11,16-17H,10,12H2,1-3H3 CC#CCOCC1=CC2=C(C=CC=C2)C(C(C(=O)OC)C(=O)OC)O1 C1=CC=C2C(=C1)C=C(OC2C(C(=O)OC)C(=O)OC)COCC#CC |(134.41,-139.61,;134.41,-151.11,;144.37,-156.86,;154.33,-151.11,;154.33,-139.61,;144.37,-133.86,;164.28,-133.86,;174.24,-139.61,;174.24,-151.11,;164.28,-156.86,;164.28,-168.36,;174.24,-174.11,;184.2,-168.36,;174.24,-185.61,;184.2,-191.36,;154.33,-174.11,;154.33,-185.61,;144.37,-168.36,;134.41,-174.11,;184.2,-133.86,;194.16,-139.61,;204.12,-133.86,;211.44,-142.73,;218.76,-151.6,;226.07,-160.48,)| AuxInfo=1/0/N:25,15,19,24,23,1,2,6,3,22,10,20,5,9,4,11,7,12,16,13,17,14,18,21,8/E:(2,3)(18,19)(20,21)(22,23)/rA:25nCCCCCCCOCCCCOOCCOOCCOCCCC/rB:d1;s2;d3;s4;s1d5;s4;s7;s8;s5d9;s7;s11;d12;s12;s14;s11;d16;s16;s18;s9;s20;s21;s22;t23;s24;/rC:134,4065,-139,6110,0;134,4065,-151,1110,0;144,3658,-156,8610,0;154,3251,-151,1110,0;154,3251,-139,6110,0;144,3658,-133,8610,0;164,2844,-156,8610,0;174,2437,-151,1110,0;174,2437,-139,6110,0;164,2844,-133,8610,0;164,2844,-168,3610,0;174,2437,-174,1110,0;184,2030,-168,3610,0;174,2437,-185,6110,0;184,2030,-191,3610,0;154,3251,-174,1110,0;154,3251,-185,6110,0;144,3658,-168,3610,0;134,4065,-174,1110,0;184,2030,-133,8610,0;194,1623,-139,6110,0;204,1216,-133,8610,0;211,4386,-142,7329,0;218,7557,-151,6048,0;226,0727,-160,4768,0; C19H20O6 COC(=O)* CO2Me,C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 25 26 0 0 0 M V30 BEGIN ATOM M V30 1 C 134.40652 -139.61102 0 0 M V30 2 C 134.40652 -151.11102 0 0 M V30 3 C 144.36581 -156.86102 0 0 M V30 4 C 154.3251 -151.11102 0 0 M V30 5 C 154.3251 -139.61102 0 0 M V30 6 C 144.36581 -133.86101 0 0 M V30 7 C 164.28439 -156.86102 0 0 M V30 8 O 174.2437 -151.11102 0 0 M V30 9 C 174.2437 -139.61102 0 0 M V30 10 C 164.28439 -133.86101 0 0 M V30 11 C 164.28439 -168.36102 0 0 M V30 12 C 174.2437 -174.11102 0 0 M V30 13 O 184.20299 -168.36102 0 0 M V30 14 O 174.24368 -185.61102 0 0 M V30 15 C 184.20299 -191.36102 0 0 M V30 16 C 154.3251 -174.11102 0 0 M V30 17 O 154.3251 -185.61102 0 0 M V30 18 O 144.36581 -168.36102 0 0 M V30 19 C 134.40652 -174.11102 0 0 M V30 20 C 184.20299 -133.86101 0 0 M V30 21 O 194.16228 -139.61102 0 0 M V30 22 C 204.12158 -133.86101 0 0 M V30 23 C 211.43861 -142.73293 0 0 M V30 24 C 218.75566 -151.60484 0 0 M V30 25 C 226.07269 -160.47676 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 4 7 M V30 8 1 7 8 M V30 9 1 8 9 M V30 10 2 9 10 M V30 11 1 10 5 M V30 12 1 7 11 M V30 13 2 12 13 M V30 14 1 12 14 M V30 15 1 14 15 M V30 16 1 11 12 M V30 17 2 16 17 M V30 18 1 16 18 M V30 19 1 18 19 M V30 20 1 11 16 M V30 21 1 9 20 M V30 22 1 20 21 M V30 23 1 21 22 M V30 24 1 22 23 M V30 25 3 23 24 M V30 26 1 24 25 M V30 END BOND M V30 END CTAB M END QRDISXGSDLMPOB-UHFFFAOYSA-N InChI=1S/C14H14O3/c1-2-3-8-17-11-14(16)9-12-6-4-5-7-13(12)10-15/h4-7,10H,8-9,11H2,1H3 CC#CCOCC(=O)CC1=C(C=CC=C1)C=O C1=CC=C(C(=C1)CC(COCC#CC)=O)C=O |(-0.25,-139.61,;-0.25,-151.11,;9.71,-156.86,;19.67,-151.11,;19.67,-139.61,;9.71,-133.86,;29.63,-133.86,;39.59,-139.61,;49.55,-133.86,;59.51,-139.61,;69.47,-133.86,;76.94,-142.59,;84.42,-151.33,;91.9,-160.07,;39.59,-151.11,;29.25,-158.36,;27.83,-169.77,)| AuxInfo=1/0/N:17,16,15,1,2,6,3,14,10,7,12,5,4,11,8,9,13/rA:17nCCCCCCCOOCCCOCCCC/rB:d1;s2;d3;s4;s1d5;s4;d7;;s5;d9s10;s11;s12;s13;s14;t15;s16;/rC:-,2500,-139,6071,0;-,2500,-151,1071,0;9,7093,-156,8571,0;19,6686,-151,1071,0;19,6686,-139,6071,0;9,7093,-133,8571,0;29,2529,-158,3571,0;27,8304,-169,7688,0;39,5872,-151,1071,0;29,6279,-133,8571,0;39,5872,-139,6071,0;49,5465,-133,8571,0;59,5058,-139,6071,0;69,4651,-133,8571,0;76,9426,-142,5942,0;84,4201,-151,3313,0;91,8976,-160,0684,0; C14H14O3 C* Me,C(=O)* CHO CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 17 17 0 0 0 M V30 BEGIN ATOM M V30 1 C -0.24998 -139.60715 0 0 M V30 2 C -0.24998 -151.10715 0 0 M V30 3 C 9.7093 -156.85715 0 0 M V30 4 C 19.66859 -151.10715 0 0 M V30 5 C 19.66859 -139.60715 0 0 M V30 6 C 9.7093 -133.85715 0 0 M V30 7 C 29.25288 -158.35715 0 0 M V30 8 O 27.83037 -169.76883 0 0 M V30 9 O 39.58717 -151.10715 0 0 M V30 10 C 29.62788 -133.85715 0 0 M V30 11 C 39.58717 -139.60715 0 0 M V30 12 C 49.54646 -133.85715 0 0 M V30 13 O 59.50577 -139.60715 0 0 M V30 14 C 69.46506 -133.85715 0 0 M V30 15 C 76.94258 -142.59424 0 0 M V30 16 C 84.4201 -151.33133 0 0 M V30 17 C 91.89761 -160.06842 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 2 7 8 M V30 8 1 4 7 M V30 9 1 5 10 M V30 10 1 10 11 M V30 11 1 11 12 M V30 12 1 12 13 M V30 13 1 13 14 M V30 14 2 11 9 M V30 15 1 14 15 M V30 16 3 15 16 M V30 17 1 16 17 M V30 END BOND M V30 END CTAB M END ZOCYPAZMSHDBID-UHFFFAOYSA-N InChI=1S/C14H12O2/c1-2-3-10-16-11-6-9-13-7-4-5-8-14(13)12-15/h4-5,7-8,12H,10-11H2,1H3 CC#CCOCC#CC1=C(C=CC=C1)C([H])=O C1=CC=C(C(=C1)C#CCOCC#CC)C([H])=O |(-0.12,-51.95,;-0.12,-63.45,;9.83,-69.2,;19.79,-63.45,;19.79,-51.95,;9.83,-46.2,;29.73,-46.22,;39.65,-40.5,;49.57,-34.78,;49.58,-23.31,;39.65,-17.56,;29.69,-23.31,;19.77,-29.03,;9.85,-34.74,;29.73,-69.19,;39.67,-63.45,;29.73,-80.67,)| AuxInfo=1/0/N:17,16,15,1,2,11,6,3,10,14,12,7,5,4,9,13/rA:17nCCCCCCCHOCCCOCCCC/rB:d1;s2;d3;s4;s1d5;s4;s7;d7;s5;t10;s11;s12;s13;s14;t15;s16;/rC:-,1250,-51,9530,0;-,1250,-63,4530,0;9,8343,-69,2030,0;19,7936,-63,4530,0;19,7936,-51,9530,0;9,8343,-46,2030,0;29,7310,-69,1904,0;39,6685,-63,4530,0;29,7310,-80,6652,0;29,7310,-46,2156,0;39,6507,-40,4992,0;49,5703,-34,7828,0;49,5796,-23,3080,0;39,6478,-17,5608,0;29,6884,-23,3108,0;19,7688,-29,0272,0;9,8492,-34,7436,0; C14H12O2 C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 17 17 0 0 0 M V30 BEGIN ATOM M V30 1 C -0.12498 -51.95297 0 0 M V30 2 C -0.12498 -63.45297 0 0 M V30 3 C 9.83427 -69.20297 0 0 M V30 4 C 19.79358 -63.45297 0 0 M V30 5 C 19.79358 -51.95297 0 0 M V30 6 C 9.83427 -46.20297 0 0 M V30 7 C 29.73105 -69.19037 0 0 M V30 8 O 29.73105 -80.66518 0 0 M V30 9 C 29.73105 -46.21558 0 0 M V30 10 C 39.65067 -40.49918 0 0 M V30 11 C 49.57028 -34.78279 0 0 M V30 12 O 49.57956 -23.30798 0 0 M V30 13 C 39.64775 -17.56082 0 0 M V30 14 C 29.68845 -23.31082 0 0 M V30 15 C 19.76883 -29.02719 0 0 M V30 16 C 9.84923 -34.74356 0 0 M V30 17 H 39.66853 -63.45297 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 4 7 M V30 8 1 7 17 M V30 9 2 7 8 M V30 10 1 5 9 M V30 11 3 9 10 M V30 12 1 10 11 M V30 13 1 11 12 M V30 14 1 12 13 M V30 15 1 13 14 M V30 16 3 14 15 M V30 17 1 15 16 M V30 END BOND M V30 END CTAB M END GAXHQDQOSREFNT-UHFFFAOYSA-N InChI=1S/C24H34O7/c1-6-9-10-11-12-17-13-16-14-19(27-4)20(28-5)15-18(16)22(31-17)21(23(25)29-7-2)24(26)30-8-3/h13-15,21-22H,6-12H2,1-5H3 CCCCCCC1=CC2=C(C=C(C(=C2)OC)OC)C(C(C(=O)OCC)C(=O)OCC)O1 C1(=C(C=C2C(=C1)C=C(OC2C(C(=O)OCC)C(=O)OCC)CCCCCC)OC)OC |(360.72,-39.14,;360.72,-50.64,;370.68,-56.39,;380.64,-50.64,;380.64,-39.14,;370.68,-33.39,;390.6,-33.39,;400.55,-39.14,;400.55,-50.64,;390.6,-56.39,;390.6,-67.89,;380.64,-73.64,;380.64,-85.14,;370.68,-67.89,;360.72,-73.64,;350.76,-67.89,;400.52,-73.62,;410.48,-67.87,;400.52,-85.12,;410.48,-90.87,;410.48,-102.37,;410.51,-33.39,;420.47,-39.14,;430.43,-33.39,;440.39,-39.14,;450.35,-33.39,;460.31,-39.14,;350.76,-56.39,;350.76,-67.89,;350.76,-33.39,;340.8,-39.14,)| AuxInfo=1/0/N:20,25,30,8,10,19,26,31,18,17,16,15,11,6,3,5,14,4,1,2,21,12,22,27,23,28,7,9,24,29,13/E:(2,3)(7,8)(23,24)(25,26)(29,30)/rA:31nCCCCCCOCOCCCOCCCCCCCCCOOCCCOOCC/rB:d1;s2;d3;s4;s1d5;s1;s7;s2;s9;s5;s4;s12;d11s13;s14;s15;s16;s17;s18;s19;s12;s21;d22;s22;;s24s25;s21;d27;s27;;s29s30;/rC:360,7177,-39,1356,0;360,7177,-50,6356,0;370,6769,-56,3856,0;380,6362,-50,6356,0;380,6362,-39,1356,0;370,6769,-33,3856,0;350,7583,-33,3856,0;340,7990,-39,1356,0;350,7583,-56,3856,0;350,7583,-67,8856,0;390,5955,-33,3856,0;390,5955,-56,3856,0;400,5548,-50,6356,0;400,5548,-39,1356,0;410,5141,-33,3857,0;420,4734,-39,1357,0;430,4327,-33,3857,0;440,3920,-39,1357,0;450,3513,-33,3857,0;460,3105,-39,1357,0;390,5955,-67,8856,0;380,6362,-73,6356,0;380,6362,-85,1356,0;370,6769,-67,8857,0;350,7583,-67,8857,0;360,7177,-73,6357,0;400,5202,-73,6157,0;410,4795,-67,8656,0;400,5202,-85,1157,0;410,4795,-102,3656,0;410,4795,-90,8656,0; C24H34O7 CCOC(=O)* CO2Et,CO* OMe,CCCCCC* (CH2)5CH3 CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 31 32 0 0 0 M V30 BEGIN ATOM M V30 1 C 360.71765 -39.13564 0 0 M V30 2 C 360.71765 -50.63564 0 0 M V30 3 C 370.67694 -56.38564 0 0 M V30 4 C 380.63623 -50.63564 0 0 M V30 5 C 380.63623 -39.13564 0 0 M V30 6 C 370.67694 -33.38564 0 0 M V30 7 O 350.75833 -33.38564 0 0 M V30 8 C 340.79904 -39.13564 0 0 M V30 9 O 350.75833 -56.38564 0 0 M V30 10 C 350.75833 -67.88564 0 0 M V30 11 C 390.59552 -33.38564 0 0 M V30 12 C 390.59546 -56.38564 0 0 M V30 13 O 400.55481 -50.63564 0 0 M V30 14 C 400.55481 -39.13564 0 0 M V30 15 C 410.5141 -33.38565 0 0 M V30 16 C 420.47339 -39.13565 0 0 M V30 17 C 430.43268 -33.38567 0 0 M V30 18 C 440.39197 -39.13568 0 0 M V30 19 C 450.35126 -33.3857 0 0 M V30 20 C 460.31055 -39.1357 0 0 M V30 21 C 390.59546 -67.88564 0 0 M V30 22 C 380.63623 -73.63564 0 0 M V30 23 O 380.63623 -85.13564 0 0 M V30 24 O 370.67691 -67.88567 0 0 M V30 25 C 350.75833 -67.8857 0 0 M V30 26 C 360.71765 -73.63568 0 0 M V30 27 C 400.5202 -73.61566 0 0 M V30 28 O 410.47949 -67.86565 0 0 M V30 29 O 400.5202 -85.11566 0 0 M V30 30 C 410.47949 -102.36565 0 0 M V30 31 C 410.47949 -90.86565 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 7 8 M V30 8 1 1 7 M V30 9 1 9 10 M V30 10 1 2 9 M V30 11 1 5 11 M V30 12 1 4 12 M V30 13 1 12 13 M V30 14 1 13 14 M V30 15 2 14 11 M V30 16 1 15 16 M V30 17 1 16 17 M V30 18 1 17 18 M V30 19 1 18 19 M V30 20 1 19 20 M V30 21 1 14 15 M V30 22 1 12 21 M V30 23 2 22 23 M V30 24 1 22 24 M V30 25 1 24 26 M V30 26 1 25 26 M V30 27 1 21 22 M V30 28 2 27 28 M V30 29 1 27 29 M V30 30 1 29 31 M V30 31 1 30 31 M V30 32 1 21 27 M V30 END BOND M V30 END CTAB M END IYXGSMUGOJNHAZ-UHFFFAOYSA-N InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3 CCOC(=O)CC(=O)OCC O(CC)C(CC(OCC)=O)=O |(189.17,-67.46,;199.08,-61.63,;209.09,-67.3,;179.17,-61.79,;169.25,-67.62,;159.25,-61.95,;149.33,-67.78,;149.43,-79.28,;139.51,-85.11,;159.15,-50.45,;179.07,-50.29,)| AuxInfo=1/0/N:2,8,3,9,5,4,6,10,11,1,7/E:(1,2)(3,4)(6,7)(8,9)(10,11)/rA:11nOCCCCCOCCOO/rB:;s1s2;s1;s4;s5;s6;;s7s8;d4;d6;/rC:189,1704,-67,4564,0;209,0883,-67,2957,0;199,0830,-61,6262,0;179,1650,-61,7870,0;169,2525,-67,6171,0;159,2471,-61,9477,0;149,3345,-67,7778,0;139,5148,-85,1076,0;149,4273,-79,2775,0;179,0723,-50,2873,0;159,1543,-50,4480,0; C7H12O4 CCO* OEt CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 11 10 0 0 0 M V30 BEGIN ATOM M V30 1 O 189.17041 -67.45641 0 0 M V30 2 C 209.08835 -67.29565 0 0 M V30 3 C 199.08298 -61.62622 0 0 M V30 4 C 179.16504 -61.78697 0 0 M V30 5 C 169.25247 -67.61714 0 0 M V30 6 C 159.2471 -61.94768 0 0 M V30 7 O 149.33453 -67.77785 0 0 M V30 8 C 139.51476 -85.10764 0 0 M V30 9 C 149.42732 -79.27747 0 0 M V30 10 O 179.07225 -50.28734 0 0 M V30 11 O 159.15431 -50.44804 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 1 1 3 M V30 2 1 2 3 M V30 3 1 4 1 M V30 4 1 5 4 M V30 5 1 6 5 M V30 6 1 7 9 M V30 7 1 8 9 M V30 8 1 7 6 M V30 9 2 4 10 M V30 10 2 6 11 M V30 END BOND M V30 END CTAB M END WVICITHMKYXHHA-UHFFFAOYSA-N InChI=1S/C17H22O3/c1-4-5-6-7-8-9-10-14-11-16(19-2)17(20-3)12-15(14)13-18/h11-13H,4-8H2,1-3H3 CCCCCCC#CC1=C(C=C(C(=C1)OC)OC)C([H])=O C1(=C(C=C(C(=C1)C#CCCCCCC)C([H])=O)OC)OC |(27.42,-50.61,;27.42,-62.11,;37.38,-67.86,;47.34,-62.11,;47.34,-50.61,;37.38,-44.86,;57.3,-44.86,;67.25,-39.11,;77.19,-33.36,;87.16,-39.11,;97.11,-33.35,;107.07,-39.1,;117.03,-33.34,;126.99,-39.09,;57.3,-67.86,;67.26,-62.11,;57.3,-79.36,;17.46,-67.86,;17.46,-79.36,;17.46,-44.86,;7.5,-50.61,)| AuxInfo=1/0/N:18,8,10,17,16,15,14,13,12,11,6,3,19,5,4,1,2,21,7,9/rA:21nCCCCCCOCOCCCCCCCCCCHO/rB:d1;s2;d3;s4;s1d5;s1;s7;s2;s9;s5;t11;s12;s13;s14;s15;s16;s17;s4;s19;d19;/rC:27,4207,-50,6134,0;27,4207,-62,1134,0;37,3800,-67,8634,0;47,3393,-62,1134,0;47,3393,-50,6134,0;37,3800,-44,8634,0;17,4614,-44,8634,0;7,5021,-50,6134,0;17,4614,-67,8634,0;17,4614,-79,3634,0;57,2986,-44,8634,0;67,2461,-39,1134,0;77,1936,-33,3634,0;87,1558,-39,1083,0;97,1121,-33,3532,0;107,0744,-39,0981,0;117,0307,-33,3430,0;126,9930,-39,0879,0;57,2986,-67,8634,0;67,2578,-62,1134,0;57,2986,-79,3634,0; C17H22O3 CO* OMe,CCCCCC* (CH2)5CH3 CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 21 21 0 0 0 M V30 BEGIN ATOM M V30 1 C 27.42067 -50.61343 0 0 M V30 2 C 27.42067 -62.11343 0 0 M V30 3 C 37.37997 -67.86343 0 0 M V30 4 C 47.33926 -62.11343 0 0 M V30 5 C 47.33926 -50.61343 0 0 M V30 6 C 37.37997 -44.86345 0 0 M V30 7 O 17.4614 -44.86345 0 0 M V30 8 C 7.50211 -50.61343 0 0 M V30 9 O 17.4614 -67.86343 0 0 M V30 10 C 17.46141 -79.36343 0 0 M V30 11 C 57.29857 -44.86345 0 0 M V30 12 C 67.24608 -39.11343 0 0 M V30 13 C 77.19356 -33.36343 0 0 M V30 14 C 87.15581 -39.10832 0 0 M V30 15 C 97.11214 -33.35321 0 0 M V30 16 C 107.07439 -39.09808 0 0 M V30 17 C 117.03072 -33.34297 0 0 M V30 18 C 126.99297 -39.08786 0 0 M V30 19 C 57.29857 -67.86343 0 0 M V30 20 O 57.29857 -79.36343 0 0 M V30 21 H 67.25784 -62.11343 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 7 8 M V30 8 1 1 7 M V30 9 1 9 10 M V30 10 1 2 9 M V30 11 1 5 11 M V30 12 3 11 12 M V30 13 1 13 14 M V30 14 1 14 15 M V30 15 1 15 16 M V30 16 1 16 17 M V30 17 1 17 18 M V30 18 1 12 13 M V30 19 1 4 19 M V30 20 1 19 21 M V30 21 2 19 20 M V30 END BOND M V30 END CTAB M END IZRLJTZDWJVNMJ-UHFFFAOYSA-N InChI=1S/C14H12O2/c1-9-6-10-4-2-3-5-11(10)14-12(9)7-16-8-13(14)15/h2-6H,7-8H2,1H3 CC1=CC2=C(C=CC=C2)C3=C1COCC3=O C1=CC=C2C(=C1)C3=C(C(=C2)C)COCC3=O |(330.79,-145.7,;330.79,-157.2,;340.75,-162.95,;350.71,-157.2,;350.71,-145.7,;340.75,-139.95,;360.67,-139.95,;370.63,-145.7,;370.63,-157.2,;360.67,-162.95,;380.59,-162.95,;380.59,-139.95,;380.59,-128.45,;370.63,-122.7,;360.67,-128.45,;350.71,-122.7,)| AuxInfo=1/0/N:16,2,1,3,6,7,11,13,8,4,5,9,14,10,15,12/rA:16nCCCCCCCCCCCOCCOC/rB:d1;s2;d3;s4;s1d5;s4;d7;s8;s5d9;s9;s11;s12;s10s13;d14;s8;/rC:330,7887,-145,6957,0;330,7887,-157,1957,0;340,7480,-162,9457,0;350,7073,-157,1957,0;350,7073,-145,6957,0;340,7480,-139,9457,0;360,6666,-162,9457,0;370,6259,-157,1957,0;370,6259,-145,6957,0;360,6666,-139,9457,0;380,5851,-139,9457,0;380,5851,-128,4457,0;370,6259,-122,6957,0;360,6666,-128,4457,0;350,7073,-122,6957,0;380,5851,-162,9457,0; C14H12O2 C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 16 18 0 0 0 M V30 BEGIN ATOM M V30 1 C 330.7887 -145.69566 0 0 M V30 2 C 330.7887 -157.19566 0 0 M V30 3 C 340.74799 -162.94566 0 0 M V30 4 C 350.70728 -157.19566 0 0 M V30 5 C 350.70728 -145.69566 0 0 M V30 6 C 340.74799 -139.94566 0 0 M V30 7 C 360.66656 -162.94566 0 0 M V30 8 C 370.62585 -157.19566 0 0 M V30 9 C 370.62585 -145.69566 0 0 M V30 10 C 360.66656 -139.94566 0 0 M V30 11 C 380.58514 -139.94566 0 0 M V30 12 O 380.58514 -128.44566 0 0 M V30 13 C 370.62585 -122.69568 0 0 M V30 14 C 360.66656 -128.44566 0 0 M V30 15 O 350.70728 -122.69568 0 0 M V30 16 C 380.58514 -162.94566 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 4 7 M V30 8 2 7 8 M V30 9 1 8 9 M V30 10 2 9 10 M V30 11 1 10 5 M V30 12 1 9 11 M V30 13 1 11 12 M V30 14 1 12 13 M V30 15 1 13 14 M V30 16 1 14 10 M V30 17 2 14 15 M V30 18 1 8 16 M V30 END BOND M V30 END CTAB M END PMTNJZPBVCGODU-LNMJFAINSA-N InChI=1S/C19H20O6/c1-18-8-9-24-10-19(18)15(18)12-7-5-4-6-11(12)14(25-19)13(16(20)22-2)17(21)23-3/h4-9,13-15H,10H2,1-3H3/t14-,15-,18-,19-/m0/s1 C[C@]12C=COC[C@@]32[C@@]1([H])C4=C(C=CC=C4)[C@@H](C(C(=O)OC)C(=O)OC)O3 C1=CC=C2C(=C1)[C@@]3([C@@]4(O[C@@H]2C(C(=O)OC)C(=O)OC)COC=C[C@@]34C)[H] |(348.84,-41.85,;348.84,-53.35,;358.8,-59.1,;368.76,-53.35,;368.76,-41.85,;358.8,-36.1,;378.71,-36.1,;388.67,-41.85,;388.67,-53.35,;378.71,-59.1,;378.71,-70.6,;368.76,-76.35,;368.76,-87.85,;358.8,-70.6,;348.84,-76.35,;388.67,-76.35,;398.63,-70.6,;388.67,-87.85,;398.63,-93.6,;398.63,-47.6,;408.59,-41.85,;408.59,-30.35,;398.63,-24.6,;388.67,-30.35,;382.92,-20.39,;368.76,-30.35,)| AuxInfo=1/0/N:16,22,26,2,1,3,6,14,13,11,4,5,17,7,10,19,23,15,9,20,24,21,25,12,8/E:(2,3)(16,17)(20,21)(22,23)/it:im/rA:26nCCCCCCC.eOC.oC.oCOCCC.oCCHCOOCCOOC/rB:d1;s2;d3;s4;s1d5;s4;s7;s8;s5s9;N9;s11;s12;d13;s9s10s14;P15;N7;N10;s17;d19;s19;s21;s17;d23;s23;s25;/rC:348,8369,-41,8472,0;348,8369,-53,3472,0;358,7961,-59,0972,0;368,7554,-53,3472,0;368,7554,-41,8472,0;358,7961,-36,0972,0;378,7147,-59,0972,0;388,6740,-53,3472,0;388,6740,-41,8472,0;378,7147,-36,0972,0;398,6333,-47,5972,0;408,5926,-41,8472,0;408,5926,-30,3472,0;398,6333,-24,5972,0;388,6740,-30,3472,0;382,9240,-20,3879,0;378,7147,-70,5972,0;368,7554,-30,3472,0;368,7554,-76,3472,0;368,7554,-87,8472,0;358,7961,-70,5972,0;348,8369,-76,3472,0;388,6740,-76,3472,0;398,6333,-70,5972,0;388,6740,-87,8472,0;398,6333,-93,5972,0; C19H20O6 COC(=O)* CO2Me,C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 26 29 0 0 1 M V30 BEGIN ATOM M V30 1 C 348.83685 -41.8472 0 0 M V30 2 C 348.83685 -53.3472 0 0 M V30 3 C 358.79614 -59.0972 0 0 M V30 4 C 368.75543 -53.3472 0 0 M V30 5 C 368.75543 -41.8472 0 0 M V30 6 C 358.79614 -36.0972 0 0 M V30 7 C 378.71472 -59.0972 0 0 CFG=1 M V30 8 O 388.67401 -53.3472 0 0 M V30 9 C 388.67401 -41.8472 0 0 CFG=1 M V30 10 C 378.71472 -36.0972 0 0 CFG=1 M V30 11 C 398.6333 -47.5972 0 0 M V30 12 O 408.59259 -41.8472 0 0 M V30 13 C 408.59259 -30.3472 0 0 M V30 14 C 398.6333 -24.5972 0 0 M V30 15 C 388.67401 -30.3472 0 0 CFG=1 M V30 16 C 382.92401 -20.38791 0 0 M V30 17 C 378.71472 -70.5972 0 0 M V30 18 C 368.75543 -76.34721 0 0 M V30 19 O 368.75543 -87.84721 0 0 M V30 20 O 358.79614 -70.59721 0 0 M V30 21 C 348.83685 -76.34721 0 0 M V30 22 C 388.67401 -76.34721 0 0 M V30 23 O 398.6333 -70.59721 0 0 M V30 24 O 388.67401 -87.84721 0 0 M V30 25 C 398.6333 -93.59721 0 0 M V30 26 H 368.75543 -30.3472 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 4 7 M V30 8 1 7 8 M V30 9 1 8 9 M V30 10 1 9 10 M V30 11 1 10 5 M V30 12 1 9 11 CFG=3 M V30 13 1 11 12 M V30 14 1 12 13 M V30 15 2 13 14 M V30 16 1 14 15 M V30 17 1 15 16 CFG=1 M V30 18 1 7 17 CFG=3 M V30 19 1 15 10 M V30 20 1 15 9 M V30 21 1 10 26 CFG=3 M V30 22 2 18 19 M V30 23 1 18 20 M V30 24 1 20 21 M V30 25 1 17 18 M V30 26 2 22 23 M V30 27 1 22 24 M V30 28 1 24 25 M V30 29 1 17 22 M V30 END BOND M V30 END CTAB M END JIEBFKOMKLAOTH-SKRQMDLTSA-N InChI=1S/C22H26O6/c1-5-7-10-14(6-2)18-15-11-8-9-12-16(15)20(28-17(18)13-23)19(21(24)26-3)22(25)27-4/h7-13,19-20,23H,5-6H2,1-4H3/b10-7+,17-13-,18-14- CC/C=C/C(=C\1/C2=C(C=CC=C2)C(C(C(=O)OC)C(=O)OC)O/C1=C\O)/CC C1=CC=C2C(=C1)C(C(=CO)OC2C(C(=O)OC)C(=O)OC)=C(C=CCC)CC |(181.31,-44.78,;181.31,-56.28,;191.27,-62.03,;201.23,-56.28,;201.23,-44.78,;191.27,-39.03,;211.19,-39.03,;221.15,-44.78,;231.11,-39.03,;241.07,-44.78,;221.15,-56.28,;211.19,-62.03,;211.19,-73.53,;221.15,-79.28,;231.11,-73.53,;221.15,-90.78,;231.11,-96.53,;201.23,-79.28,;201.23,-90.78,;191.27,-73.53,;181.31,-79.28,;211.19,-27.53,;221.15,-21.78,;231.11,-27.53,;241.07,-21.78,;251.05,-27.55,;201.23,-21.78,;191.25,-27.55,)| AuxInfo=1/0/N:20,18,24,28,19,14,11,1,2,12,6,3,9,13,5,4,8,7,17,15,21,25,10,22,26,23,27,16/E:(3,4)(21,22)(24,25)(26,27)/rA:28nCCCCCCCCCOCCCCCOCCCCCOOCCOOC/rB:d1;s2;d3;s4;s1d5;s5;s7;d+8;s9;;d+11;d+7s12;s13;s4;s8s15;s15;s14;s11;s19;s17;d21;s21;s23;s17;d25;s25;s27;/rC:181,3111,-44,7833,0;181,3111,-56,2833,0;191,2704,-62,0333,0;201,2297,-56,2833,0;201,2297,-44,7833,0;191,2704,-39,0333,0;211,1890,-39,0333,0;221,1483,-44,7833,0;231,1075,-39,0333,0;241,0668,-44,7833,0;231,1076,-27,5333,0;221,1483,-21,7833,0;211,1890,-27,5333,0;201,2297,-21,7833,0;211,1890,-62,0333,0;221,1483,-56,2833,0;211,1890,-73,5333,0;191,2485,-27,5460,0;241,0668,-21,7833,0;251,0480,-27,5460,0;221,1483,-79,2833,0;231,1076,-73,5333,0;221,1483,-90,7833,0;231,1076,-96,5333,0;201,2297,-79,2833,0;201,2297,-90,7833,0;191,2704,-73,5333,0;181,3111,-79,2833,0; C22H26O6 COC(=O)* CO2Me,C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 28 29 0 0 0 M V30 BEGIN ATOM M V30 1 C 181.3111 -44.78334 0 0 M V30 2 C 181.3111 -56.28334 0 0 M V30 3 C 191.27039 -62.03334 0 0 M V30 4 C 201.22968 -56.28334 0 0 M V30 5 C 201.22968 -44.78334 0 0 M V30 6 C 191.27039 -39.03334 0 0 M V30 7 C 211.18896 -39.03334 0 0 M V30 8 C 221.14825 -44.78334 0 0 M V30 9 C 231.10754 -39.03334 0 0 M V30 10 O 241.06685 -44.78334 0 0 M V30 11 C 231.10756 -27.53334 0 0 M V30 12 C 221.14825 -21.78334 0 0 M V30 13 C 211.18896 -27.53334 0 0 M V30 14 C 201.22968 -21.78334 0 0 M V30 15 C 211.18896 -62.03334 0 0 M V30 16 O 221.14825 -56.28334 0 0 M V30 17 C 211.18896 -73.53334 0 0 M V30 18 C 191.24852 -27.54596 0 0 M V30 19 C 241.06685 -21.78334 0 0 M V30 20 C 251.048 -27.54596 0 0 M V30 21 C 221.14825 -79.28334 0 0 M V30 22 O 231.10756 -73.53334 0 0 M V30 23 O 221.14827 -90.78334 0 0 M V30 24 C 231.10756 -96.53334 0 0 M V30 25 C 201.22968 -79.28334 0 0 M V30 26 O 201.22968 -90.78334 0 0 M V30 27 O 191.27039 -73.53334 0 0 M V30 28 C 181.3111 -79.28334 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 5 7 M V30 8 1 7 8 M V30 9 2 8 9 M V30 10 1 9 10 M V30 11 2 11 12 M V30 12 1 12 13 M V30 13 1 13 14 M V30 14 1 4 15 M V30 15 1 15 16 M V30 16 1 15 17 M V30 17 1 14 18 M V30 18 1 11 19 M V30 19 1 19 20 M V30 20 1 16 8 M V30 21 2 7 13 M V30 22 2 21 22 M V30 23 1 21 23 M V30 24 1 23 24 M V30 25 1 17 21 M V30 26 2 25 26 M V30 27 1 25 27 M V30 28 1 27 28 M V30 29 1 17 25 M V30 END BOND M V30 END CTAB M END LVEBUSOTCALOQM-UHFFFAOYSA-N InChI=1S/C22H26O6/c1-5-12-11-13(6-2)18(23)20-16(12)14-9-7-8-10-15(14)19(28-20)17(21(24)26-3)22(25)27-4/h7-11,13,17-19,23H,5-6H2,1-4H3 CCC1=CC([H])(CC)C(C2=C1C3=C(C=CC=C3)C(C(C(=O)OC)C(=O)OC)O2)O C1=CC=C2C(=C1)C3=C(C(O)C(C=C3CC)(CC)[H])OC2C(C(=O)OC)C(=O)OC |(279.1,-44.89,;279.1,-56.39,;289.06,-62.14,;299.02,-56.39,;299.02,-44.89,;289.06,-39.14,;308.98,-39.14,;318.94,-44.89,;328.9,-39.14,;338.86,-44.89,;328.9,-27.64,;318.94,-21.89,;308.98,-27.64,;299.02,-21.89,;289.04,-27.65,;338.86,-21.89,;348.84,-27.65,;328.9,-16.12,;318.94,-56.39,;308.98,-62.14,;308.98,-73.64,;318.94,-79.39,;328.9,-73.64,;318.94,-90.89,;328.9,-96.64,;299.02,-79.39,;299.02,-90.89,;289.06,-73.64,;279.1,-79.39,)| AuxInfo=1/0/N:18,20,24,28,14,19,1,2,6,3,12,13,11,5,4,7,17,9,15,8,21,25,10,22,26,23,27,16/E:(3,4)(21,22)(24,25)(26,27)/rA:29nCCCCCCCCCOCCCCCOCCCCCOOCCOOCH/rB:d1;s2;d3;s4;s1d5;s5;d7;s8;s9;s9;s11;s7d12;s13;s4;s8s15;s15;s14;s11;s19;s17;d21;s21;s23;s17;d25;s25;s27;s11;/rC:279,1010,-44,8912,0;279,1010,-56,3912,0;289,0603,-62,1412,0;299,0196,-56,3912,0;299,0196,-44,8912,0;289,0603,-39,1412,0;308,9789,-39,1412,0;318,9382,-44,8912,0;328,8975,-39,1412,0;338,8568,-44,8912,0;328,8975,-27,6412,0;318,9382,-21,8912,0;308,9789,-27,6412,0;299,0196,-21,8912,0;308,9789,-62,1412,0;318,9382,-56,3912,0;308,9789,-73,6412,0;289,0384,-27,6538,0;338,8568,-21,8912,0;348,8379,-27,6538,0;318,9382,-79,3912,0;328,8975,-73,6412,0;318,9382,-90,8912,0;328,8975,-96,6412,0;299,0196,-79,3912,0;299,0196,-90,8912,0;289,0603,-73,6412,0;279,1010,-79,3912,0;328,8975,-16,1159,0; C22H26O6 COC(=O)* CO2Me,C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 29 31 0 0 0 M V30 BEGIN ATOM M V30 1 C 279.10098 -44.89117 0 0 M V30 2 C 279.10098 -56.39117 0 0 M V30 3 C 289.0603 -62.14117 0 0 M V30 4 C 299.01959 -56.39117 0 0 M V30 5 C 299.01959 -44.89117 0 0 M V30 6 C 289.0603 -39.14116 0 0 M V30 7 C 308.97888 -39.14116 0 0 M V30 8 C 318.93817 -44.89117 0 0 M V30 9 C 328.89746 -39.14116 0 0 M V30 10 O 338.85675 -44.89117 0 0 M V30 11 C 328.89746 -27.64117 0 0 M V30 12 C 318.93817 -21.89117 0 0 M V30 13 C 308.97888 -27.64117 0 0 M V30 14 C 299.01959 -21.89117 0 0 M V30 15 C 308.97888 -62.14117 0 0 M V30 16 O 318.93817 -56.39117 0 0 M V30 17 C 308.97888 -73.64117 0 0 M V30 18 C 289.03842 -27.65379 0 0 M V30 19 C 338.85675 -21.89117 0 0 M V30 20 C 348.83789 -27.65379 0 0 M V30 21 C 318.93817 -79.39117 0 0 M V30 22 O 328.89746 -73.64117 0 0 M V30 23 O 318.93817 -90.89117 0 0 M V30 24 C 328.89746 -96.64117 0 0 M V30 25 C 299.01959 -79.39117 0 0 M V30 26 O 299.01959 -90.89117 0 0 M V30 27 O 289.0603 -73.64117 0 0 M V30 28 C 279.10101 -79.39117 0 0 M V30 29 H 328.89746 -16.11592 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 5 7 M V30 8 2 7 8 M V30 9 1 8 9 M V30 10 1 9 10 M V30 11 1 11 12 M V30 12 2 12 13 M V30 13 1 13 14 M V30 14 1 4 15 M V30 15 1 15 16 M V30 16 1 15 17 M V30 17 1 14 18 M V30 18 1 11 19 M V30 19 1 19 20 M V30 20 1 16 8 M V30 21 1 7 13 M V30 22 1 9 11 M V30 23 2 21 22 M V30 24 1 21 23 M V30 25 1 23 24 M V30 26 1 17 21 M V30 27 2 25 26 M V30 28 1 25 27 M V30 29 1 27 28 M V30 30 1 17 25 M V30 31 1 11 29 M V30 END BOND M V30 END CTAB M END NVLZWKHRGCZKNK-UHFFFAOYSA-N InChI=1S/C22H24O5/c1-5-13-11-14(6-2)18-15-9-7-8-10-16(15)20(27-17(18)12-13)19(21(23)25-3)22(24)26-4/h7-12,19-20H,5-6H2,1-4H3 CCC1=CC2=C(C(=C1)CC)C3=CC=CC=C3C(C(C(=O)OC)C(=O)OC)O2 C1=CC=C2C(=C1)C3=C(OC2C(C(=O)OC)C(=O)OC)C=C(C=C3CC)CC |(382.36,-44.94,;382.36,-56.46,;392.34,-62.22,;402.32,-56.46,;402.32,-44.94,;392.34,-39.17,;412.3,-39.17,;422.28,-44.94,;422.28,-56.46,;412.3,-62.22,;412.3,-73.72,;402.34,-79.47,;402.34,-90.97,;392.38,-73.72,;382.42,-79.47,;422.26,-79.47,;432.22,-73.72,;422.26,-90.97,;432.22,-96.72,;432.26,-39.17,;432.26,-27.65,;422.28,-21.88,;412.3,-27.65,;402.34,-21.9,;392.38,-27.65,;442.22,-21.9,;452.18,-27.65,)| AuxInfo=1/0/N:17,19,23,27,16,18,1,2,6,3,14,12,13,15,5,4,9,10,11,7,20,24,21,25,22,26,8/E:(3,4)(21,22)(23,24)(25,26)/rA:27nCCCCCCCOCCCCCCCCCCCCOOCCOOC/rB:d1;s2;d3;s4;s1d5;s4;s7;s8;s5d9;s7;s9;d12;s13;s10d14;s13;s16;s15;s18;s11;d20;s20;s22;s11;d24;s24;s26;/rC:382,3591,-44,9351,0;382,3591,-56,4604,0;392,3403,-62,2230,0;402,3214,-56,4604,0;402,3214,-44,9351,0;392,3403,-39,1725,0;412,3026,-62,2230,0;422,2837,-56,4604,0;422,2837,-44,9351,0;412,3026,-39,1725,0;412,3026,-73,7230,0;432,2649,-39,1725,0;432,2649,-27,6472,0;422,2837,-21,8846,0;412,3026,-27,6472,0;442,2242,-21,8972,0;452,1835,-27,6472,0;402,3433,-21,8972,0;392,3840,-27,6472,0;402,3433,-79,4730,0;402,3433,-90,9730,0;392,3840,-73,7230,0;382,4247,-79,4730,0;422,2618,-79,4730,0;432,2211,-73,7230,0;422,2618,-90,9730,0;432,2211,-96,7230,0; C22H24O5 COC(=O)* CO2Me,C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 27 29 0 0 0 M V30 BEGIN ATOM M V30 1 C 382.35913 -44.93512 0 0 M V30 2 C 382.35913 -56.46036 0 0 M V30 3 C 392.34027 -62.22298 0 0 M V30 4 C 402.32141 -56.46036 0 0 M V30 5 C 402.32141 -44.93512 0 0 M V30 6 C 392.34027 -39.1725 0 0 M V30 7 C 412.30255 -62.22298 0 0 M V30 8 O 422.28372 -56.46036 0 0 M V30 9 C 422.28372 -44.93512 0 0 M V30 10 C 412.30255 -39.1725 0 0 M V30 11 C 412.30255 -73.72298 0 0 M V30 12 C 432.26489 -39.1725 0 0 M V30 13 C 432.26489 -27.64725 0 0 M V30 14 C 422.28372 -21.88461 0 0 M V30 15 C 412.30255 -27.64725 0 0 M V30 16 C 442.22418 -21.89725 0 0 M V30 17 C 452.18347 -27.64725 0 0 M V30 18 C 402.34326 -21.89725 0 0 M V30 19 C 392.38397 -27.64725 0 0 M V30 20 C 402.34326 -79.47298 0 0 M V30 21 O 402.34326 -90.97298 0 0 M V30 22 O 392.38397 -73.72298 0 0 M V30 23 C 382.42468 -79.47296 0 0 M V30 24 C 422.26184 -79.47298 0 0 M V30 25 O 432.22113 -73.72298 0 0 M V30 26 O 422.26184 -90.97298 0 0 M V30 27 C 432.22113 -96.72298 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 4 7 M V30 8 1 7 8 M V30 9 1 8 9 M V30 10 2 9 10 M V30 11 1 10 5 M V30 12 1 7 11 M V30 13 1 9 12 M V30 14 2 12 13 M V30 15 1 13 14 M V30 16 2 14 15 M V30 17 1 15 10 M V30 18 1 13 16 M V30 19 1 16 17 M V30 20 1 15 18 M V30 21 1 18 19 M V30 22 2 20 21 M V30 23 1 20 22 M V30 24 1 22 23 M V30 25 1 11 20 M V30 26 2 24 25 M V30 27 1 24 26 M V30 28 1 26 27 M V30 29 1 11 24 M V30 END BOND M V30 END CTAB M END OSRVDVQTZHBGON-FHTBDLFWSA-N InChI=1S/C22H26O6/c1-5-13-11-14(6-2)27-12-17-18(13)15-9-7-8-10-16(15)20(28-17)19(21(23)25-3)22(24)26-4/h7-12,14,18-20H,5-6H2,1-4H3/t14-,18?,20?/m1/s1 CCC1=C[C@@H](CC)OC=C2C1([H])C3=C(C=CC=C3)C(C(C(=O)OC)C(=O)OC)O2 C1=CC=C2C(=C1)C3(C(=CO[C@@H](C=C3CC)CC)OC2C(C(=O)OC)C(=O)OC)[H] |(97.49,-54.04,;97.49,-65.54,;107.45,-71.29,;117.41,-65.54,;117.41,-54.04,;107.45,-48.29,;127.37,-48.29,;137.33,-54.04,;148.03,-49.84,;151.42,-38.85,;144.94,-29.35,;133.47,-28.49,;125.65,-36.92,;114.66,-33.53,;112.1,-22.32,;150.69,-19.39,;144.94,-9.43,;137.33,-65.54,;127.37,-71.29,;127.37,-82.79,;137.33,-88.54,;147.28,-82.79,;137.33,-100.04,;147.28,-105.79,;117.41,-88.54,;117.41,-100.04,;107.45,-82.79,;97.49,-88.54,;116.23,-45.31,)| AuxInfo=1/0/N:18,20,25,29,14,19,1,2,6,3,12,9,13,11,5,4,8,7,17,15,22,26,23,27,24,28,10,16/E:(3,4)(21,22)(23,24)(25,26)/it:im/rA:29nCCCCCCCCCOC.oCCCCOCCCCHCOOCCOOC/rB:d1;s2;d3;s4;s1d5;s5;s7;d8;s9;s10;s11;s7d12;s13;s4;s8s15;s15;s14;P11;s19;s7;s17;d22;s22;s24;s17;d26;s26;s28;/rC:97,4883,-54,0397,0;97,4883,-65,5397,0;107,4475,-71,2897,0;117,4068,-65,5397,0;117,4068,-54,0397,0;107,4475,-48,2897,0;127,3661,-48,2897,0;137,3254,-54,0397,0;148,0305,-49,8383,0;151,4202,-38,8492,0;144,9420,-29,3475,0;133,4741,-28,4881,0;125,6521,-36,9182,0;114,6631,-33,5285,0;127,3661,-71,2897,0;137,3254,-65,5397,0;127,3661,-82,7897,0;112,1040,-22,3168,0;150,6920,-19,3882,0;144,9420,-9,4289,0;116,2336,-45,3068,0;137,3254,-88,5397,0;147,2847,-82,7897,0;137,3254,-100,0397,0;147,2847,-105,7897,0;117,4068,-88,5397,0;117,4068,-100,0397,0;107,4475,-82,7897,0;97,4882,-88,5397,0; C22H26O6 COC(=O)* CO2Me,C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 29 31 0 0 1 M V30 BEGIN ATOM M V30 1 C 97.48825 -54.03975 0 0 M V30 2 C 97.48825 -65.53975 0 0 M V30 3 C 107.44754 -71.28975 0 0 M V30 4 C 117.40685 -65.53975 0 0 M V30 5 C 117.40685 -54.03975 0 0 M V30 6 C 107.44754 -48.28975 0 0 M V30 7 C 127.36613 -48.28975 0 0 M V30 8 C 137.32542 -54.03975 0 0 M V30 9 C 148.03046 -49.83833 0 0 M V30 10 O 151.42015 -38.84923 0 0 M V30 11 C 144.94197 -29.34749 0 0 CFG=2 M V30 12 C 133.47412 -28.4881 0 0 M V30 13 C 125.65215 -36.9182 0 0 M V30 14 C 114.66306 -33.5285 0 0 M V30 15 C 127.36613 -71.28975 0 0 M V30 16 O 137.32542 -65.53975 0 0 M V30 17 C 127.36613 -82.78975 0 0 M V30 18 C 112.10405 -22.31685 0 0 M V30 19 C 150.69197 -19.3882 0 0 M V30 20 C 144.94197 -9.42891 0 0 M V30 21 C 137.32542 -88.53975 0 0 M V30 22 O 147.28471 -82.78975 0 0 M V30 23 O 137.32542 -100.03975 0 0 M V30 24 C 147.28471 -105.78975 0 0 M V30 25 C 117.40683 -88.53975 0 0 M V30 26 O 117.40681 -100.03975 0 0 M V30 27 O 107.44754 -82.78975 0 0 M V30 28 C 97.48824 -88.53973 0 0 M V30 29 H 116.2336 -45.30678 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 5 7 M V30 8 1 7 8 M V30 9 2 8 9 M V30 10 1 9 10 M V30 11 1 10 11 M V30 12 1 11 12 M V30 13 2 12 13 M V30 14 1 13 14 M V30 15 1 4 15 M V30 16 1 15 16 M V30 17 1 15 17 M V30 18 1 14 18 M V30 19 1 11 19 CFG=1 M V30 20 1 19 20 M V30 21 1 16 8 M V30 22 1 7 13 M V30 23 1 7 29 M V30 24 2 21 22 M V30 25 1 21 23 M V30 26 1 23 24 M V30 27 1 17 21 M V30 28 2 25 26 M V30 29 1 25 27 M V30 30 1 27 28 M V30 31 1 17 25 M V30 END BOND M V30 END CTAB M END QOTGWWZNRLLAKZ-CAZDACIESA-L InChI=1S/C22H26O6.2ClH.Pt/c1-5-13-11-14(6-2)27-12-17-18(13)15-9-7-8-10-16(15)20(28-17)19(21(23)25-3)22(24)26-4;;;/h7-10,14,18-20H,5-6,12H2,1-4H3;2*1H;/q+1;;;+1/p-2/t14-,18?,20?;;;/m1.../s1 CCC1=C([C@@H](CC)OC([H])C2=[O+]C(C3=C(C=CC=C3)C12)C(C(=O)OC)C(=O)OC)[Pt-](Cl)Cl C1=CC=C2C(=C1)C3C(C(O[C@@H](C(=C3CC)[Pt-](Cl)Cl)CC)[H])=[O+]C2C(C(=O)OC)C(=O)OC |(7,-54.67,;7,-66.17,;16.96,-71.92,;26.92,-66.17,;26.92,-54.67,;16.96,-48.92,;36.88,-48.92,;46.84,-54.67,;57.55,-50.47,;60.93,-39.48,;54.46,-29.98,;42.99,-29.12,;35.17,-37.55,;24.18,-34.16,;16.03,-42.31,;38.79,-18.41,;45.96,-9.42,;27.42,-16.7,;60.21,-20.02,;54.46,-10.06,;65.69,-58.62,;46.84,-66.17,;36.88,-71.92,;36.88,-83.42,;46.84,-89.17,;56.8,-83.42,;46.84,-100.67,;56.8,-106.42,;26.92,-89.17,;26.92,-100.67,;16.96,-83.42,;7,-89.17,)| AuxInfo=1/1/N:18,20,28,32,14,19,1,2,6,3,12,9,13,11,5,4,8,7,17,15,25,29,26,30,27,31,10,16;22;23;21/E:(3,4)(21,22)(23,24)(25,26);;;/it:im;;;/CRV:11.3,28+1;;;/rA:32nCCCCCCCCCOC.oCCCCO+CCCCPt-ClClHCOOCCOOC/rB:d1;s2;d3;s4;s1d5;s5;s7;s8;s9;s10;s11;s7d12;s13;s4;d8s15;s15;s14;P11;s19;s12;s21;s21;s9;s17;d25;s25;s27;s17;d29;s29;s31;/rC:7,0029,-54,6716,0;7,0029,-66,1716,0;16,9622,-71,9216,0;26,9215,-66,1716,0;26,9215,-54,6716,0;16,9622,-48,9216,0;36,8808,-48,9216,0;46,8401,-54,6716,0;57,5451,-50,4702,0;60,9348,-39,4811,0;54,4566,-29,9794,0;42,9888,-29,1200,0;35,1668,-37,5501,0;24,1777,-34,1604,0;36,8808,-71,9216,0;46,8401,-66,1716,0;36,8808,-83,4216,0;16,0281,-42,3100,0;60,2066,-20,0201,0;54,4566,-10,0608,0;38,7873,-18,4149,0;45,9575,-9,4238,0;27,4158,-16,7009,0;65,6947,-58,6198,0;46,8401,-89,1716,0;56,7993,-83,4216,0;46,8401,-100,6716,0;56,7994,-106,4216,0;26,9215,-89,1716,0;26,9215,-100,6716,0;16,9622,-83,4216,0;7,0029,-89,1716,0; C22H26Cl2O6Pt Cl[Pt-](Cl)* PtCl2,COC(=O)* CO2Me,C* Me CDK 04232617462D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 32 34 0 0 1 M V30 BEGIN ATOM M V30 1 C 7.00288 -54.67163 0 0 M V30 2 C 7.00288 -66.17162 0 0 M V30 3 C 16.96217 -71.92162 0 0 M V30 4 C 26.92148 -66.17162 0 0 M V30 5 C 26.92148 -54.67163 0 0 M V30 6 C 16.96217 -48.92162 0 0 M V30 7 C 36.88077 -48.92162 0 0 M V30 8 C 46.84006 -54.67163 0 0 M V30 9 C 57.5451 -50.4702 0 0 M V30 10 O 60.93478 -39.48111 0 0 M V30 11 C 54.4566 -29.97937 0 0 CFG=2 M V30 12 C 42.98877 -29.11996 0 0 M V30 13 C 35.16679 -37.55006 0 0 M V30 14 C 24.17769 -34.16037 0 0 M V30 15 C 36.88077 -71.92162 0 0 M V30 16 O 46.84006 -66.17162 0 0 CHG=1 M V30 17 C 36.88077 -83.42163 0 0 M V30 18 C 16.02812 -42.30995 0 0 M V30 19 C 60.2066 -20.02008 0 0 M V30 20 C 54.4566 -10.06079 0 0 M V30 21 Pt 38.78734 -18.41492 0 0 CHG=-1 M V30 22 Cl 45.95747 -9.42384 0 0 M V30 23 Cl 27.41579 -16.70093 0 0 M V30 24 C 46.84006 -89.17162 0 0 M V30 25 O 56.79935 -83.42162 0 0 M V30 26 O 46.84006 -100.67162 0 0 M V30 27 C 56.79936 -106.42162 0 0 M V30 28 C 26.92148 -89.17162 0 0 M V30 29 O 26.92148 -100.67162 0 0 M V30 30 O 16.96219 -83.42162 0 0 M V30 31 C 7.0029 -89.17162 0 0 M V30 32 H 65.69469 -58.61977 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 5 7 M V30 8 1 7 8 M V30 9 1 8 9 M V30 10 1 9 10 M V30 11 1 10 11 M V30 12 1 11 12 M V30 13 2 12 13 M V30 14 1 13 14 M V30 15 1 4 15 M V30 16 1 15 16 M V30 17 1 15 17 M V30 18 1 14 18 M V30 19 1 11 19 CFG=1 M V30 20 1 19 20 M V30 21 2 16 8 M V30 22 1 7 13 M V30 23 1 21 22 M V30 24 1 21 23 M V30 25 1 12 21 M V30 26 1 9 32 M V30 27 2 24 25 M V30 28 1 24 26 M V30 29 1 26 27 M V30 30 1 17 24 M V30 31 2 28 29 M V30 32 1 28 30 M V30 33 1 30 31 M V30 34 1 17 28 M V30 END BOND M V30 END CTAB M END Characterization data, spectra, and crystal structure data. Financial support from the NIGMS (P41 GM076263 and P50 GM067041) is gratefully acknowledged. We thank Professors John Snyder, Scott Schaus, and James Panek (Boston University) for helpful discussions. Org. Lett. J. Org. Chem. Org. Lett. J. Am. Chem. Soc. J. Am. Chem. Soc. Proc. Natl. Acad. Sci. U. S. A. Org. Lett. See for gold-catalyzed cycloisomerization of o -alkynylbenzaldehydes with a pendant alkyne. Angew. Chem., Int. Ed. See for a review of cycloisomerizations. Angew. Chem., Int. Ed. Angew. Chem., Int. Ed. J. Org. Chem. See for Cu(I)-mediated cycloisomerization/alcohol addition of an o -alkynylbenzaldehyde. Org. Lett. See for Cu(I)-mediated cycloisomerization. J. Am. Chem. Soc. Chem.–Eur. J. Org. Lett. Angew. Chem., Int. Ed. Org. Lett. ChemCatChem Tetrahedron Angew. Chem., Int. Ed. J. Org. Chem. Eur. J. Org. Chem. J. Org. Chem. Chem.–Eur. J. Adv. Synth. Catal. ACS Comb. Sci. See for an illustrative recent application of cycloisomerizations in diversity-oriented synthesis (DOS). 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