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Search for "tartaric acid" in Full Text gives 36 result(s) in Beilstein Journal of Organic Chemistry.
Hybrid macrocycle formation and spiro annulation on cis-syn-cis-tricyclo[6.3.0.02,6]undeca-3,11-dione and its congeners via ring-closing metathesis
- Sambasivarao Kotha,
- Ajay Kumar Chinnam and
- Rashid Ali
Beilstein J. Org. Chem. 2015, 11, 1123–1128, doi:10.3762/bjoc.11.126
- shown that Weiss–Cook dione 1 [49][50][51] is a useful substrate for double Fischer indolization with a low melting mixture of L-(+)-tartaric acid and N,N′-dimethylurea (L-(+)-TA:DMU) [55] at 70 °C to generate an unusual Cs-symmetric diindole derivative along with the known C2-symmetric diindole [56
Graphical Abstract
Figure 1: Natural and non-natural products containing quinane systems.
Figure 2: Quinane building blocks (1–3) and metathetic catalyst used in our strategy.
Scheme 1: Synthesis of tricyclic diones 5 and 2.
Figure 3: Retrosynthetic approach to aza-polyquinane 6 and spiro-polyquinane 7.
Scheme 2: Synthesis of the diindole derivative 9 Reagents and conditions: (i) TA:DMU, PhNHNH3Cl, 70 °C, 6 h, ...
Scheme 3: Synthesis of the macrocyclic aza-polyquinane derivative 6. Reagents and conditions: (i) NaH, allyl ...
Scheme 4: Synthesis of the spiro-polyquinane 7. Reagents and conditions: (i) NaH, allyl bromide, THF, rt, 24 ...
Scheme 5: General strategy to bis-spirocycles via RCM.
Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
- Carolin Edinger,
- Jörn Kulisch and
- Siegfried R. Waldvogel
Beilstein J. Org. Chem. 2015, 11, 294–301, doi:10.3762/bjoc.11.34
- by enantiomeric resolution employing tartaric acid (see Scheme 2, pathway IV) [43]. By the amount of water in the crystallisation mixture the precipitation of the desired diastereomeric salt can be chosen [44]. Furthermore, we developed a Bouveault–Blanc-type protocol where (−)-menthone oxime is
Graphical Abstract
Scheme 1: Structural features of 8-substituted menthylamines 1.
Scheme 2: Synthetic strategies to menthylamines.
Scheme 3: Stereoselective synthesis of 8-substituted (1R,3R,4S)-menthylamines.
Scheme 4: Influence of the cathode system onto the stereoselectivity of the reduction of (1R,4S)-menthone oxi...
Scheme 5: Preparation of 8-substituted (1R)-menthones 6 and the corresponding oximes 7.
Scheme 6: Influence of cathode material on the preparation of (1R,3R,4S)-menthylamine 8a.
Scheme 7: Protection of the oxime functionality in 7c due to the sterically demanding diphenyl moiety in 8-po...
Scheme 8: Separation of the diastereomeric 8-substituted menthylamines by crystallization of their hydrochlor...
An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles
- Marcus Baumann and
- Ian R. Baxendale
Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265
- ). The required (R)-enantiomer of ethyl nipecotate can in turn be obtained by a number of different methods including the resolution of the racemate using L-(+)-tartaric acid obtained from full saturation of ethyl nicotinate. More modern methods involve a two-step process wherein ethyl nicotinate (2.52
- isolation of enaminoester 2.80 after treatment of the intermediate with ammonium acetate in methanol. The next step involves a very efficient crystallisation-induced dynamic resolution of the racemic material using the non-natural (S,S)-dibenzoyl-D-tartaric acid ((+)-DBTA). It is described that the desired
Graphical Abstract
Scheme 1: Scaled industrial processes for the synthesis of simple pyridines.
Scheme 2: Synthesis of nicotinic acid from 2-methyl-5-ethylpyridine (1.11).
Scheme 3: Synthesis of 3-picoline and nicotinic acid.
Scheme 4: Synthesis of 3-picoline from 2-methylglutarodinitrile 1.19.
Scheme 5: Picoline-based synthesis of clarinex (no yields reported).
Scheme 6: Mode of action of proton-pump inhibitors and structures of the API’s.
Scheme 7: Hantzsch-like route towards the pyridine rings in common proton pump inhibitors.
Figure 1: Structures of rosiglitazone (1.40) and pioglitazone (1.41).
Scheme 8: Synthesis of rosiglitazone.
Scheme 9: Syntheses of 2-pyridones.
Scheme 10: Synthesis and mechanism of 2-pyrone from malic acid.
Scheme 11: Polymer-assisted synthesis of rosiglitazone.
Scheme 12: Synthesis of pioglitazone.
Scheme 13: Meerwein arylation reaction towards pioglitazone.
Scheme 14: Route towards pioglitazone utilising tyrosine.
Scheme 15: Route towards pioglitazone via Darzens ester formation.
Scheme 16: Syntheses of the thiazolidinedione moiety.
Scheme 17: Synthesis of etoricoxib utilising Negishi and Stille cross-coupling reactions.
Scheme 18: Synthesis of etoricoxib via vinamidinium condensation.
Figure 2: Structures of nalidixic acid, levofloxacin and moxifloxacin.
Scheme 19: Synthesis of moxifloxacin.
Scheme 20: Synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane 1.105.
Scheme 21: Synthesis of levofloxacin.
Scheme 22: Alternative approach to the levofloxacin core 1.125.
Figure 3: Structures of nifedipine, amlodipine and clevidipine.
Scheme 23: Mg3N2-mediated synthesis of nifedipine.
Scheme 24: Synthesis of rac-amlodipine as besylate salt.
Scheme 25: Aza Diels–Alder approach towards amlodipine.
Scheme 26: Routes towards clevidipine.
Figure 4: Examples of piperidine containing drugs.
Figure 5: Discovery of tiagabine based on early leads.
Scheme 27: Synthetic sequences to tiagabine.
Figure 6: Structures of solifenacin (2.57) and muscarine (2.58).
Scheme 28: Enantioselective synthesis of solifenacin.
Figure 7: Structures of DPP-4 inhibitors of the gliptin-type.
Scheme 29: Formation of inactive diketopiperazines from cis-rotameric precursors.
Figure 8: Co-crystal structure of carmegliptin bound in the human DPP-4 active site (PDB 3kwf).
Scheme 30: Improved route to carmegliptin.
Figure 9: Structures of lamivudine and zidovudine.
Scheme 31: Typical routes accessing uracil, thymine and cytosine.
Scheme 32: Coupling between pyrimidones and riboses via the Vorbrüggen nucleosidation.
Scheme 33: Synthesis of lamivudine.
Scheme 34: Synthesis of raltegravir.
Scheme 35: Mechanistic studies on the formation of 3.22.
Figure 10: Structures of selected pyrimidine containing drugs.
Scheme 36: General preparation of pyrimidines and dihydropyrimidones.
Scheme 37: Synthesis of imatinib.
Scheme 38: Flow synthesis of imatinib.
Scheme 39: Syntheses of erlotinib.
Scheme 40: Synthesis of erlotinib proceeding via Dimroth rearrangement.
Scheme 41: Synthesis of lapatinib.
Scheme 42: Synthesis of rosuvastatin.
Scheme 43: Alternative preparation of the key aldehyde towards rosuvastatin.
Figure 11: Structure comparison between nicotinic acetylcholine receptor agonists.
Scheme 44: Syntheses of varenicline and its key building block 4.5.
Scheme 45: Synthetic access to eszopiclone and brimonidine via quinoxaline intermediates.
Figure 12: Bortezomib bound in an active site of the yeast 20S proteasome ([114], pdb 2F16).
Scheme 46: Asymmetric synthesis of bortezomib.
Figure 13: Structures of some prominent piperazine containing drugs.
Figure 14: Structural comparison between the core of aplaviroc (4.35) and a type-1 β-turn (4.36).
Scheme 47: Examplary synthesis of an aplaviroc analogue via the Ugi-MCR.
Scheme 48: Syntheses of azelastine (5.1).
Figure 15: Structures of captopril, enalapril and cilazapril.
Scheme 49: Synthesis of cilazapril.
Figure 16: Structures of lamotrigine, ceftriaxone and azapropazone.
Scheme 50: Synthesis of lamotrigine.
Scheme 51: Alternative synthesis of lamotrigine (no yields reported).
Figure 17: Structural comparison between imiquimod and the related adenosine nucleoside.
Scheme 52: Conventional synthesis of imiquimod (no yields reported).
Scheme 53: Synthesis of imiquimod.
Scheme 54: Synthesis of imiquimod via tetrazole formation (not all yields reported).
Figure 18: Structures of various anti HIV-medications.
Scheme 55: Synthesis of abacavir.
Figure 19: Structures of diazepam compared to modern replacements.
Scheme 56: Synthesis of ocinaplon.
Scheme 57: Access to zaleplon and indiplon.
Scheme 58: Different routes towards the required N-methylpyrazole 6.65 of sildenafil.
Scheme 59: Polymer-supported reagents in the synthesis of key aminopyrazole 6.72.
Scheme 60: Early synthetic route to sildenafil.
Scheme 61: Convergent preparations of sildenafil.
Figure 20: Comparison of the structures of sildenafil, tadalafil and vardenafil.
Scheme 62: Short route to imidazotriazinones.
Scheme 63: Alternative route towards vardenafils core imidazotriazinone (6.95).
Scheme 64: Bayer’s approach to the vardenafil core.
Scheme 65: Large scale synthesis of vardenafil.
Scheme 66: Mode of action of temozolomide (6.105) as methylating agent.
Scheme 67: Different routes to temozolomide.
Scheme 68: Safer route towards temozolomide.
Figure 21: Some unreported heterocyclic scaffolds in top market drugs.
Asymmetric synthesis of host-directed inhibitors of myxoviruses
- Terry W. Moore,
- Kasinath Sana,
- Dan Yan,
- Pahk Thepchatri,
- John M. Ndungu,
- Manohar T. Saindane,
- Mark A. Lockwood,
- Michael G. Natchus,
- Dennis C. Liotta,
- Richard K. Plemper,
- James P. Snyder and
- Aiming Sun
Beilstein J. Org. Chem. 2013, 9, 197–203, doi:10.3762/bjoc.9.23
- ) had the poorest antiviral activity (i.e., 18a and 18e, Table 1). To explore the possibility of increasing solubility by salt formation, the L-tartaric acid salt and benzenesulfonic acid salts of the most active compound 18f were synthesized (Figure 3) and subjected to solubility testing. However
- )- (left, magenta) and (R)- (right, cyan) enantiomers of 1. L-Tartaric acid salt (18f-tartrate) and benzenesulfonic acid salt (18f-benzenesulfonate) of 18f. Synthesis of anilino nitrobenzene 7a. Preparation of morpholinyl-o-nitroanilines. Asymmetric synthesis of (R)- and (S)-isomers by using two different
Graphical Abstract
Figure 1: Structure of first-generation lead compound 1.
Scheme 1: Synthesis of anilino nitrobenzene 7a.
Scheme 2: Preparation of morpholinyl-o-nitroanilines.
Scheme 3: Asymmetric synthesis of (R)- and (S)-isomers by using two different approaches.
Scheme 4: Preparation of chiral propionamides by HATU-mediated coupling (a) or thionyl chloride-mediated coup...
Figure 2: Renderings of crystal structures of (S)- (left, magenta) and (R)- (right, cyan) enantiomers of 1.
Figure 3: L-Tartaric acid salt (18f-tartrate) and benzenesulfonic acid salt (18f-benzenesulfonate) of 18f.
Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics
- Marco Marradi,
- Stefano Cicchi,
- Francesco Sansone,
- Alessandro Casnati and
- Andrea Goti
Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107
- -tartaric acid) [28], and its functional groups (an anchoring amine and two transformable hydroxy groups) make it a convenient chiral AB2 building block for the construction of dendrimers [29]. The linkable hydroxy groups of the pyrrolidine rings open up the possibility of constructing calixarene-based
Graphical Abstract
Figure 1: First (2) and second (3) generation of dendrimers based on chiral C2-symmetric pyrrolidine 1 and ha...
Scheme 1: Use of the key intermediate (3S,4S)-1-benzyl-3,4-dihydroxypyrrolidine (6) [31] for the synthesis of pyr...
Scheme 2: Synthesis of calixarene-based dendrimers 2 and 3. Reagents and conditions: DIPEA, CH2Cl2, 30 °C, 5 ...
Figure 2: Expansion (about 7 to 3 ppm) of the 1H NMR spectra of (A) the free ligand 2, (B) the sodium picrate...
Figure 3: Schematic of the inclusion of alkali-metal ions (sodium and potassium) in the polar cavity defined ...
A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
- Nianhong Lu,
- Lihong Wang,
- Zhanshan Li and
- Wei Zhang
Beilstein J. Org. Chem. 2012, 8, 192–200, doi:10.3762/bjoc.8.21
- -alkenylboronates with 2-ethoxy-N-acylquinolines catalyzed by tartaric acid to produce 2-(1-alkenyl)-N-acylquinolines in 2011 [23]. We report here a concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the cross-coupling reactions of N-acyliminium ions derived from 3-hydroxyisoindol
Graphical Abstract
Scheme 1: Reaction of 3-hydroxyisoindol-1-one with styrene.
Scheme 2: Reaction of 5-hydroxypyrrol-1-one with styrene.
Scheme 3: Reactions of 5-hydroxyisoindol-1-ones with olefins in the presence of BF3·OEt2.
Figure 1: X-Ray structure (ORTEP drawing) of 3h.
Scheme 4: Reactions of 5-hydroxypyrrol-1-ones with olefins in the presence of BF3·OEt2.
An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals
- Marcus Baumann,
- Ian R. Baxendale,
- Steven V. Ley and
- Nikzad Nikbin
Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57
Graphical Abstract
Figure 1: Structures of atorvastatin and other commercial statins.
Figure 2: Structure of compactin.
Scheme 1: Synthesis of pentasubstituted pyrroles.
Scheme 2: [3 + 2] Cycloaddition to prepare 5-isopropylpyrroles.
Scheme 3: Regiospecific [3 + 2] cycloaddition to prepare the pyrrole scaffold.
Scheme 4: Formation of the pyrrole core of atorvastatin via [3 + 2] cycloaddition.
Scheme 5: Formation of pyrrole 33 via the Paal–Knorr reaction.
Scheme 6: Convergent synthesis towards atorvastatin.
Figure 3: Binding pocket of sunitinib in the TRK KIT.
Scheme 7: Synthesis of sunitinib.
Scheme 8: Alternative synthesis of sunitinib.
Scheme 9: Key steps in the syntheses of sumatriptan and zolmitriptan.
Scheme 10: Introduction of the N,N-dimethylaminoethyl side chain.
Scheme 11: Japp–Klingemann reaction in the synthesis of sumatriptan.
Scheme 12: Synthesis of the intermediate sulfonyl chlorides 62 and 63.
Scheme 13: Alternative introduction of the sulfonamide.
Scheme 14: Negishi-type coupling to benzylic sulfonamides.
Scheme 15: Heck reaction used to introduce the sulfonamide side chain of naratriptan.
Scheme 16: Synthesis of the oxazolinone appendage of zolmitriptan.
Scheme 17: Grandberg indole synthesis used in the preparation of rizatriptan.
Scheme 18: Improved synthesis of rizatriptan.
Scheme 19: Larock-type synthesis of rizatriptan.
Scheme 20: Synthesis of eletriptan.
Scheme 21: Heck coupling for the indole system in eletriptan.
Scheme 22: Attempted Fischer indole synthesis of elatriptan.
Scheme 23: Successful Fischer indole synthesis for eletriptan.
Scheme 24: Mechanistic rationale for the Bischler–Möhlau reaction.
Scheme 25: Bischler-type indole synthesis used in the fluvastatin sodium synthesis.
Scheme 26: Palladium-mediated synthesis of ondansetron.
Scheme 27: Fischer indole synthesis of ondansetron.
Scheme 28: Optimised Pictet–Spengler reaction towards tadalafil.
Figure 4: Structures of carvedilol 136 and propranolol 137.
Scheme 29: Synthesis of the carbazole core of carvedilol.
Scheme 30: Alternative syntheses of 4-hydroxy-9H-carbazole.
Scheme 31: Convergent synthesis of etodolac.
Scheme 32: Alternative synthesis of etodolac.
Figure 5: Structures of imidazole-containing drugs.
Scheme 33: Synthesis of functionalised imidazoles towards losartan.
Scheme 34: Direct synthesis of the chlorinated imidazole in losartan.
Scheme 35: Synthesis of trisubstituted imidazoles.
Scheme 36: Preparation of the imidazole ring in olmesartan.
Scheme 37: Synthesis of ondansetron.
Scheme 38: Alternative route to ondansetron and its analogues.
Scheme 39: Proton pump inhibitors and synthesis of esomeprazole.
Scheme 40: Synthesis of benzimidazole core pantoprazole.
Figure 6: Structure of rabeprazole 194.
Scheme 41: Synthesis of candesartan.
Scheme 42: Alternative access to the candesartan key intermediate 216.
Scheme 43: .Medicinal chemistry route to telmisartan.
Scheme 44: Improved synthesis of telmisartan.
Scheme 45: Synthesis of zolpidem.
Scheme 46: Copper-catalysed 3-component coupling towards zolpidem.
Figure 7: Structure of celecoxib.
Scheme 47: Preparation of celecoxib.
Scheme 48: Alternative synthesis of celecoxib.
Scheme 49: Regioselective access to celecoxib.
Scheme 50: Synthesis of pazopanib.
Scheme 51: Syntheses of anastrozole, rizatriptan and letrozole.
Scheme 52: Regioselective synthesis of anastrozole.
Scheme 53: Triazine-mediated triazole formation towards anastrozole.
Scheme 54: Alternative routes to 1,2,4-triazoles.
Scheme 55: Initial synthetic route to sitagliptin.
Figure 8: Binding of sitagliptin within DPP-IV.
Scheme 56: The process route to sitagliptin key intermediate 280.
Scheme 57: Synthesis of maraviroc.
Scheme 58: Synthesis of alprazolam.
Scheme 59: The use of N-nitrosoamidine derivatives in the preparation of fused benzodiazepines.
Figure 9: Structures of itraconazole, ravuconazole and voriconazole.
Scheme 60: Synthesis of itraconazole.
Scheme 61: Synthesis of rufinamide.
Scheme 62: Representative tetrazole formation in valsartan.
Figure 10: Structure of tetrazole containing olmesartan, candesartan and irbesartan.
Scheme 63: Early stage introduction of the tetrazole in losartan.
Scheme 64: Synthesis of cilostazol.
Figure 11: Structure of cefdinir.
Scheme 65: Semi-synthesis of cefdinir.
Scheme 66: Thiazole syntheses towards ritonavir.
Scheme 67: Synthesis towards pramipexole.
Scheme 68: Alternative route to pramipexole.
Scheme 69: Synthesis of famotidine.
Scheme 70: Efficient synthesis of the hyperuricemic febuxostat.
Scheme 71: Synthesis of ziprasidone.
Figure 12: Structure of mometasone.
Scheme 72: Industrial access to 2-furoic acid present in mometasone.
Scheme 73: Synthesis of ranitidine from furfuryl alcohol.
Scheme 74: Synthesis of nitrofurantoin.
Scheme 75: Synthesis of benzofuran.
Scheme 76: Synthesis of amiodarone.
Scheme 77: Synthesis of raloxifene.
Scheme 78: Alternative access to the benzo[b]thiophene core of raloxifene.
Scheme 79: Gewald reaction in the synthesis of olanzapine.
Scheme 80: Alternative synthesis of olanzapine.
Figure 13: Access to simple thiophene-containing drugs.
Scheme 81: Synthesis of clopidogrel.
Scheme 82: Pictet–Spengler reaction in the preparation of tetrahydrothieno[3,2-c]pyridine (422).
Scheme 83: Alternative synthesis of key intermediate 422.
Figure 14: Co-crystal structures of timolol (left) and carazolol (right) in the β-adrenergic receptor.
Scheme 84: Synthesis of timolol.
Scheme 85: Synthesis of tizanidine 440.
Scheme 86: Synthesis of leflunomide.
Scheme 87: Synthesis of sulfamethoxazole.
Scheme 88: Synthesis of risperidone.
Figure 15: Relative abundance of selected transformations.
Figure 16: The abundance of heterocycles within top 200 drugs (5-membered rings).
Rh-Catalyzed rearrangement of vinylcyclopropane to 1,3-diene units attached to N-heterocycles
- Franca M. Cordero,
- Carolina Vurchio,
- Stefano Cicchi,
- Armin de Meijere and
- Alberto Brandi
Beilstein J. Org. Chem. 2011, 7, 298–303, doi:10.3762/bjoc.7.39
- the enantiopure nitrone 10 [42] derived from L-tartaric acid was complete within only 1.5 h at 120–125 °C under microwave (MW) heating and afforded the oxospirocyclopropanes anti-12 and syn-12 in 55% overall yield along with the 1,5-hydrogen shift product 13 (13%) (Scheme 3, see Supporting Information
Graphical Abstract
Scheme 1: General approach to spirocyclopropanated tetrahydropyridones by 1,3-dipolar cycloaddition/thermal r...
Scheme 2: Synthesis of tetrahydrospiro[cyclopropane-1,1’(2’H,6’H)-pyrido[2,1-a]isoquinolin]-2’-one 8.
Scheme 3: Synthesis of 7’-oxohexahydro spiro[cyclopropane-1-8’(5’H)indolizines] 12.
Scheme 4: Olefination of spirocyclopropanated heterocyclic ketones 8, 12 and 16.
Figure 1: Key NOE interactions. 18: 11b-H/11-H, 11b-H/6-H, 11b-H/Ht, Hv/2-CH3; E-19: Hb/CH3, Hc/11b-H, Hc/11-...
Scheme 5: Rearrangement of VCPs 15 and 17 catalyzed by Rh(PPh3)3Cl.
Scheme 6: Mechanism of the rearrangement of heterocyclic VCPs catalyzed by Rh(PPh3)3Cl.
Quinoline based receptor in fluorometric discrimination of carboxylic acids
- Kumaresh Ghosh,
- Suman Adhikari,
- Asoke P. Chattopadhyay and
- Purnendu Roy Chowdhury
Beilstein J. Org. Chem. 2008, 4, No. 52, doi:10.3762/bjoc.4.52
- reduced. The change in absorbance with complex concentration is found to be linear (Figure 4, right side). Figure 5 indicates the case of 1 with D-(−)-tartaric acid where a similar nature of interaction is attributed. These changes in the UV-vis spectra were used conveniently to study the binding since
- the same guests were carried out in CHCl3. The change in absorbance of the complexes of 2 with the acid guests on dilution with CHCl3 was linear in each case. Figure 6 and Figure 7, for example, demonstrate the changes in absorbance of the 1:1 complexes of citric acid and D-(−)-tartaric acid
- -(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absorbance on dilution (left side); plot of absorbance vs. concentration of the complex of D-(−)-tartaric acid with 1 (right side). UV spectra of the complex of 2 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on dilution (left side
Graphical Abstract
Figure 1: Structures of compounds 1 and 2.
Scheme 1: Syntheses of receptors 1 and 2.
Figure 2: UV-vis spectra of 1 (c = 5.05 × 10−5 M) in different solvents.
Figure 3: UV-vis spectra of 2 (c = 5.05 × 10−5 M) in different solvents.
Figure 4: UV spectra of the complex of 1 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on...
Figure 5: UV spectra of the complex of 1 with D-(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absor...
Figure 6: UV spectra of the complex of 2 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on...
Figure 7: UV spectra of the complex of 2 with D-(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absor...
Figure 8: Fluorescence change of 1 in CHCl3 in the presence of carboxylic acids (λex = 290 nm).
Figure 9: Plot of the ratio of excimer to monomer emission vs concentration of the complex of 1 with citric a...
Figure 10: Fluorescence change of 1 in CHCl3 (c = 1.67 × 10−5 M) upon addition of citric acid dissolved in CHCl...
Figure 11: Fluorescence change of 1 in CHCl3 (c = 1.67 × 10−5 M) upon addition of D-(−)-tartaric acid dissolve...
Figure 12: Fluorescence change of 2 in CHCl3 in the presence of carboxylic acids (λex = 290 nm).
Figure 13: Fluorescence change of 2 in CHCl3 (c = 1.67 × 10−5 M) upon addition citric acid dissolved in CHCl3 ...
Figure 14: 1H NMR (in CDCl3) spectra of receptor 1 (c = 3.57 × 10−3 M; bottom) and the 1:1 complex with citric...
Figure 15: AM1 optimized geometries of the complexes of 1 with (a) citric acid, hydrogen bond distances: a = 2...
Figure 16: AM1 optimized geometry of the complex of 2 with citric acid, hydrogen bond distances: a = 2.12 Å, b...
Recent progress on the total synthesis of acetogenins from Annonaceae
- Nianguang Li,
- Zhihao Shi,
- Yuping Tang,
- Jianwei Chen and
- Xiang Li
Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48
- materials (e.g. amino acids, sugars, tartaric acid, etc.) or on asymmetric reactions {e.g. Sharpless asymmetric epoxidation (AE), Sharpless asymmetric dihydroxylation (AD), diastereoselective Williamson etherification, etc.}. Semi-synthesis of natural ACGs as well as derivatised ACGs (e.g. amines, esters
Graphical Abstract
Scheme 1: Total synthesis of longifolicin by Marshall’s group.
Scheme 2: Total synthesis of corossoline by Tanaka’s group.
Scheme 3: Total synthesis of corossoline by Wu’s group.
Scheme 4: Total synthesis of pseudo-annonacin A by Hanessian’s group.
Scheme 5: Total synthesis of tonkinecin by Wu’s group.
Scheme 6: Total synthesis of gigantetrocin A by Shi’s group.
Scheme 7: Total synthesis of annonacin by Wu’s group.
Scheme 8: Total synthesis of solamin by Kitahara’s group.
Scheme 9: Total synthesis of solamin by Mioskowski’s group.
Scheme 10: Total synthesis of cis-solamin by Makabe’s group.
Scheme 11: Total synthesis of cis-solamin by Brown’s group.
Scheme 12: The formal synthesis of (+)-cis-solamin by Donohoe’s group.
Scheme 13: Total synthesis of cis-solamin by Stark’s group.
Scheme 14: Total synthesis of mosin B by Tanaka’s group.
Scheme 15: Total synthesis of longicin by Hanessian’s group.
Scheme 16: Total synthesis of murisolin and 16,19-cis-murisolin by Tanaka’s group.
Scheme 17: Synthesis of a stereoisomer library of (+)-murisolin by Curran’s group.
Scheme 18: Total synthesis of murisolin by Makabe’s group.
Scheme 19: Total synthesis of reticulatain-1 by Makabe’s group.
Scheme 20: Total synthesis of muricatetrocin C by Ley’s group.
Scheme 21: Total synthesis of (4R,12S,15S,16S,19R,20R,34S)-muricatetrocin (146) and (4R,12R,15S,16S,19R,20R,34S...
Scheme 22: Total synthesis of parviflorin by Hoye’s group.
Scheme 23: Total synthesis of parviflorin by Trost’s group.
Scheme 24: Total synthesis of trilobacin by Sinha’s group.
Scheme 25: Total synthesis of 15-epi-annonin I 181b by Scharf’s group.
Scheme 26: Total synthesis of squamocin A and squamocin D by Scharf’s group.
Scheme 27: Total synthesis of asiminocin by Marshall’s group.
Scheme 28: Total synthesis of asiminecin by Marshall’s group.
Scheme 29: Total synthesis of (+)-(30S)-bullanin by Marshall’s group.
Scheme 30: Total synthesis of uvaricin by the group of Sinha and Keinan.
Scheme 31: Formal synthesis of uvaricin by Burke’s group.
Scheme 32: Total synthesis of trilobin by Marshall’s group.
Scheme 33: Total synthesis of trilobin by the group of Sinha and Keinan.
Scheme 34: Total synthesis of asimilobin by the group of Wang and Shi.
Scheme 35: Total synthesis of squamotacin by the group of Sinha and Keinan.
Scheme 36: Total synthesis of asimicin by Marshall’s group.
Scheme 37: Total synthesis of asimicin by the group of Sinha and Keinan.
Scheme 38: Total synthesis of asimicin by Roush’s group.
Scheme 39: Total synthesis of asimicin by Marshall’s group.
Scheme 40: Total synthesis of 10-hydroxyasimicin by Ley’s group.
Scheme 41: Total synthesis of asimin by Marshall’s group.
Scheme 42: Total synthesis of bullatacin by the group of Sinha and Keinan.
Scheme 43: Total synthesis of bullatacin by Roush’s group.
Scheme 44: Total synthesis of bullatacin by Pagenkopf’s group.
Scheme 45: Total synthesis of rollidecins C and D by the group of Sinha and Keinan.
Scheme 46: Total synthesis of 30(S)-hydroxybullatacin by Marshall’s group.
Scheme 47: Total synthesis of uvarigrandin A and 5(R)-uvarigrandin A by Marshall’s group.
Scheme 48: Total synthesis of membranacin by Brown’s group.
Scheme 49: Total synthesis of membranacin by Lee’s group.
Scheme 50: Total synthesis of rolliniastatin 1 and rollimembrin by Lee’s group.
Scheme 51: Total synthesis of longimicin D by the group of Maezaki and Tanaka.
Scheme 52: Total synthesis of the structure proposed for mucoxin by Borhan’s group.
Scheme 53: Modular synthesis of adjacent bis-THF annonaceous acetogenins by Marshall’s group.
Scheme 54: Total synthesis of 4-deoxygigantecin by Tanaka’s group.
Scheme 55: Total synthesis of squamostatins D by Marshall’s group.
Scheme 56: Total synthesis of gigantecin by Crimmins’s group.
Scheme 57: Total synthesis of gigantecin by Hoye’s group.
Scheme 58: Total synthesis of cis-sylvaticin by Donohoe’s group.
Scheme 59: Total synthesis of 17(S),18(S)-goniocin by Sinha’s group.
Scheme 60: Total synthesis of goniocin and cyclogoniodenin T by the group of Sinha and Keinan.
Scheme 61: Total synthesis of jimenezin by Takahashi’s group.
Scheme 62: Total synthesis of jimenezin by Lee’s group.
Scheme 63: Total synthesis of jimenezin by Hoffmann’s group.
Scheme 64: Total synthesis of muconin by Jacobsen’s group.
Scheme 65: Total synthesis of (+)-muconin by Kitahara’s group.
Scheme 66: Total synthesis of muconin by Takahashi’s group.
Scheme 67: Total synthesis of muconin by the group of Yoshimitsu and Nagaoka.
Scheme 68: Total synthesis of mucocin by the group of Sinha and Keinan.
Scheme 69: Total synthesis of mucocin by Takahashi’s group.
Scheme 70: Total synthesis of (−)-mucocin by Koert’s group.
Scheme 71: Total synthesis of mucocin by the group of Takahashi and Nakata.
Scheme 72: Total synthesis of mucocin by Evans’s group.
Scheme 73: Total synthesis of mucocin by Mootoo’s group.
Scheme 74: Total synthesis of (−)-mucocin by Crimmins’s group.
Scheme 75: Total synthesis of pyranicin by the group of Takahashi and Nakata.
Scheme 76: Total synthesis of pyranicin by Rein’s group.
Scheme 77: Total synthesis of proposed pyragonicin by the group of Takahashi and Nakata.
Scheme 78: Total synthesis of pyragonicin by Rein’s group.
Scheme 79: Total synthesis of pyragonicin by Takahashi’s group.
Scheme 80: Total synthesis of squamostanal A by Figadère’s group.
Scheme 81: Total synthesis of diepomuricanin by Tanaka’s group.
Scheme 82: Total synthesis of (−)-muricatacin [(R,R)-373a] and its enantiomer (+)-muricatacin [(S,S)-373b] by ...
Scheme 83: Total synthesis of epi-muricatacin (+)-(S,R)-373c and (−)-(R,S)-373d by Scharf’s group.
Scheme 84: Total synthesis of (−)-muricatacin 373a and 5-epi-(−)-muricatacin 373d by Uang’s group.
Scheme 85: Total synthesis of four stereoisomers of muricatacin by Yoon’s group.
Scheme 86: Total synthesis of (+)-muricatacin by Figadère’s group.
Scheme 87: Total synthesis of (+)-epi-muricatacin and (−)-muricatacin by Couladouros’s group.
Scheme 88: Total synthesis of muricatacin by Trost’s group.
Scheme 89: Total synthesis of (−)-(4R,5R)-muricatacin by Heck and Mioskowski’s group.
Scheme 90: Total synthesis of muricatacin (−)-373a by the group of Carda and Marco.
Scheme 91: Total synthesis of (−)- and (+)-muricatacin by Popsavin’s group.
Scheme 92: Total synthesis of (−)-muricatacin by the group of Bernard and Piras.
Scheme 93: Total synthesis of (−)-muricatacin by the group of Yoshimitsu and Nagaoka.
Scheme 94: Total synthesis of (−)-muricatacin by Quinn’s group.
Scheme 95: Total synthesis of montecristin by Brückner’s group.
Scheme 96: Total synthesis of (−)-acaterin by the group of Franck and Figadère.
Scheme 97: Total synthesis of (−)-acaterin by Singh’s group.
Scheme 98: Total synthesis of (−)-acaterin by Kumar’s group.
Scheme 99: Total synthesis of rollicosin by Quinn’s group.
Scheme 100: Total synthesis of Rollicosin by Makabe’s group.
Scheme 101: Total synthesis of squamostolide by Makabe’s group.
Scheme 102: Total synthesis of tonkinelin by Makabe’s group.
C2- symmetric bisamidines: Chiral Brønsted bases catalysing the Diels- Alder reaction of anthrones
- Deniz Akalay,
- Gerd Dürner,
- Jan W. Bats and
- Michael W. Göbel
Beilstein J. Org. Chem. 2008, 4, No. 28, doi:10.3762/bjoc.4.28
- extraction in the presence of Na2CO3 afforded the neutral bases 8b–c and ent-8d in almost quantitative yield. The S,S configurated diamines 9b and 9c were prepared from L-(+)-tartaric acid (R,R) via the vicinal diazide using Saalfrank's procedure [9]. 9d was purchased as the dihydrochloride salt and then
Graphical Abstract
Scheme 1: Diels-Alder reaction of anthrones 1 and maleimides 2 catalyzed by chiral Brønsted bases 4–8.
Scheme 2: Protonation states and tautomerism of C2-symmetric bisamidine 8a [6].
Scheme 3: Synthesis of C2-symmetric bisamidines 8b–c and ent-8d.
Figure 1: Kinetic measurements of 1a with 2a catalyzed by 5 mol% of 8a·H+·TFPB- (black line) and 1 mol% 8a (f...
Figure 2: Molecular structure of 3m (C: black; N: blue; O: red; Cl: green; hydrogen atoms are omitted for the...
Scheme 4: Proposed mechanism of the Diels-Alder reaction.
