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Search for "fredericamycin" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.
Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis
- Lihua Wei,
- Rui Yang,
- Zhifeng Shi and
- Zhiqiang Ma
Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151
- ) in 83% yield. Candida rugosa lipase (CRL) The lipase CRL from Candida rugosa, another species of Candida genus, was used by the Kita group in their asymmetric synthesis of fredericamycin A in 2005 (Scheme 8) [39]. Different from their previous strategy [40] constructing the spiro chiral center via
- enantioenriched monoester 53 in hand, the synthesis proceeded toward fredericamycin A (60) (Scheme 9). Dione 55, which was prepared from 53 in six steps, underwent addition with alkyne 56 followed by acylation of the resulting hydroxy group with compound 57 to yield ketone 58. A subsequent seven-step
- synthesis of fredericamycin A (60). Takabe’s synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (64). Takabe’s synthesis of (18S)-variabilin (70). Kawasaki’s synthesis of (S)-Rosaphen (74) and (R)-Rosaphen (75). Tokuyama’s synthesis of a) (−)-petrosin (84) and b) (+)-petrosin (86). Fukuyama’s synthesis of
Graphical Abstract
Scheme 1: General mechanism of a lipase-catalyzed esterification.
Scheme 2: Shishido’s synthesis of (−)-xanthorrhizol (4) and (+)-heliannuol D (8).
Scheme 3: Shishido’s synthesis of a) (−)-heliannuol A (15) and b) heliannuol G (20) and heliannuol H (21).
Scheme 4: Deska’s synthesis of hyperione A (30) and ent-hyperione B (31).
Scheme 5: Huang’s synthesis of (+)-brazilin (37).
Scheme 6: Shishido’s synthesis of (−)-heliannuol D (42) and (+)-heliannuol A (43).
Scheme 7: Chênevert’s synthesis of (S)-α-tocotrienol (49).
Scheme 8: Kita’s synthesis of monoester 53.
Scheme 9: Kita’s synthesis of fredericamycin A (60).
Scheme 10: Takabe’s synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (64).
Scheme 11: Takabe’s synthesis of (18S)-variabilin (70).
Scheme 12: Kawasaki’s synthesis of (S)-Rosaphen (74) and (R)-Rosaphen (75).
Scheme 13: Tokuyama’s synthesis of a) (−)-petrosin (84) and b) (+)-petrosin (86).
Scheme 14: Fukuyama’s synthesis of leustroducsin B (96).
Scheme 15: Nanda’s synthesis of a) fragment 100, b) fragment 106 and c) (−)-rasfonin (109).
Scheme 16: Davies’ synthesis of (+)-pilocarpine (115) and (+)-isopilocarpine (116).
Scheme 17: Ōmura’s synthesis of salinosporamide A (125).
Scheme 18: Kang’s synthesis of ʟ-cladinose (124) and its derivative.
Scheme 19: Kang’s preparation of fragment 139.
Scheme 20: Kang’s synthesis of azithromycin (149).
Scheme 21: Kang’s synthesis of (−)-dysiherbaine (156).
Scheme 22: Kang’s synthesis of (−)-kaitocephalin (166).
Scheme 23: Kang’s synthesis of laidlomycin (180).
Scheme 24: Snyder’s synthesis of arboridinine (190).
Scheme 25: Ma’s synthesis of (+)-alstrostine G (203).
Scheme 26: Trost’s synthesis of (−)-18-epi-peloruside A (215).
Scheme 27: Lindel’s synthesis of (–)-dihydroraputindole (223).
Scheme 28: Iwata’s synthesis of a) (−)-talaromycin B (232) and b) (+)-talaromycin A (235).
Scheme 29: Cook’s synthesis of a) (−)-vincamajinine (240) and b) (−)-11-methoxy-17-epivincamajine (245).
Scheme 30: Cook’s synthesis of (+)-dehydrovoachalotine (249) and voachalotine (250).
Scheme 31: Cook’s synthesis of a) (−)-12-methoxy-Nb-methylvoachalotine (257) and b) (+)-polyneuridine, macusin...
Scheme 32: Trauner’s synthesis of stephadiamine (273).
Scheme 33: Garg’s synthesis of (–)-ψ-akuammigine (285).
Scheme 34: Ding’s synthesis of (+)-18-benzoyldavisinol (293) and (+)-davisinol (294).
Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds
- Alemayehu Gashaw Woldegiorgis and
- Xufeng Lin
Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185
- ., fredericamycin A and acutumine [99]), SPINOL-based ligands and catalysts [100], and organometallic complexes with important applications. The use of chiral catalysts for spirocyclization reactions brings asymmetry at the site of the spirocyclic center while tolerating different electronic and steric functional
Graphical Abstract
Figure 1: Representative examples of axially chiral biaryls, heterobiaryls, spiranes and allenes as ligands a...
Figure 2: Selected examples of axially chiral drugs and bioactive molecules.
Figure 3: Axially chiral functional materials and supramolecules.
Figure 4: Important chiral phosphoric acid scaffolds used in this review.
Scheme 1: Atroposelective aryl–aryl-bond formation by employing a facile [3,3]-sigmatropic rearrangement.
Scheme 2: Atroposelective synthesis of axially chiral biaryl amino alcohols 5.
Scheme 3: The enantioselective reaction of quinone and 2-naphthol derivatives.
Scheme 4: Enantioselective synthesis of multisubstituted biaryls.
Scheme 5: Enantioselective synthesis of axially chiral quinoline-derived biaryl atropisomers mediated by chir...
Scheme 6: Pd-Catalyzed atroposelective C–H olefination of biarylamines.
Scheme 7: Palladium-catalyzed directed atroposelective C–H allylation.
Scheme 8: Enantioselective synthesis of axially chiral (a) aryl indoles and (b) biaryldiols.
Scheme 9: Asymmetric arylation of indoles enabled by azo groups.
Scheme 10: Proposed mechanism for the asymmetric arylation of indoles.
Scheme 11: Enantioselective synthesis of axially chiral N-arylindoles [38].
Scheme 12: Enantioselective [3 + 2] formal cycloaddition and central-to-axial chirality conversion.
Scheme 13: Organocatalytic atroposelective arene functionalization of nitrosonaphthalene with indoles.
Scheme 14: Proposed reaction mechanism for the atroposelective arene functionalization of nitrosonaphthalenes.
Scheme 15: Asymmetric construction of axially chiral naphthylindoles [65].
Scheme 16: Enantioselective synthesis of axially chiral 3,3’-bisindoles [66].
Scheme 17: Atroposelective synthesis of 3,3’-bisiindoles bearing axial and central chirality.
Scheme 18: Enantioselective synthesis of axially chiral 3,3’-bisindoles bearing single axial chirality.
Scheme 19: Enantioselective reaction of azonaphthalenes with various pyrazolones.
Scheme 20: Enantioselective and atroposelective synthesis of axially chiral N-arylcarbazoles [73].
Scheme 21: Atroposelective cyclodehydration reaction.
Scheme 22: Atroposelective construction of axially chiral N-arylbenzimidazoles [78].
Scheme 23: Proposed reaction mechanism for the atroposelective synthesis of axially chiral N-arylbenzimidazole...
Scheme 24: Atroposelective synthesis of axially chiral arylpyrroles [21].
Scheme 25: Synthesis of axially chiral arylquinazolinones and its reaction pathway [35].
Scheme 26: Synthesis of axially chiral aryquinoline by Friedländer heteroannulation reaction and its proposed...
Scheme 27: Povarov cycloaddition–oxidative chirality conversion process.
Scheme 28: Atroposelective synthesis of oxindole-based axially chiral styrenes via kinetic resolution.
Scheme 29: Synthesis of axially chiral alkene-indole frame works [45].
Scheme 30: Proposed reaction mechanism for axially chiral alkene-indoles.
Scheme 31: Atroposelective C–H aminations of N-aryl-2-naphthylamines with azodicarboxylates.
Scheme 32: Synthesis of brominated atropisomeric N-arylquinoids.
Scheme 33: The enantioselective syntheses of axially chiral SPINOL derivatives.
Scheme 34: γ-Addition reaction of various 2,3-disubstituted indoles to β,γ-alkynyl-α-imino esters.
Scheme 35: Regio- and stereoselective γ-addition reactions of isoxazol-5(4H)-ones to β,γ-alkynyl-α-imino ester...
Scheme 36: Synthesis of chiral tetrasubstituted allenes and naphthopyrans.
Scheme 37: Asymmetric remote 1,8-conjugate additions of thiazolones and azlactones to propargyl alcohols.
Scheme 38: Synthesis of chiral allenes from 1-substituted 2-naphthols [107].
Directed aromatic functionalization in natural-product synthesis: Fredericamycin A, nothapodytine B, and topopyrones B and D
- Charles Dylan Turner and
- Marco A. Ciufolini
Beilstein J. Org. Chem. 2011, 7, 1475–1485, doi:10.3762/bjoc.7.171
- activity: Fredericamycin A, nothapodytine B, and topopyrones B and D. In each case, directed aromatic functionalization methodology greatly facilitated the assembly of the key molecular subunits. Keywords: alkaloids; directed aromatic functionalization; fredericamycin; heterocyclic compounds; lithiation
- specific synthetic endeavors in our group. Herein, we illustrate the application of such techniques to three representative problems that we have addressed over the years: The syntheses of fredericamycin A, nothapodytine B, and topopyrones B and D. Fredericamycin A This initial portion of the present
- review recounts the first project that the senior author of this paper launched as an independent academic in 1984. A structurally novel natural product by the name of fredericamycin A (1, Scheme 1) had been discovered only two years prior and determined to be strongly cytotoxic [1][2][3][4][5]: A
Graphical Abstract
Scheme 1: Structure and retrosynthetic analysis of fredericamycin A.
Scheme 2: Assembly of the isoquinolone segment of fredericamycin.
Scheme 3: Synthesis of a naphthalide precursor to the quinoid moiety of fredericamycin.
Scheme 4: Palladium-mediated cyclization of a fredericamycin model system.
Scheme 5: Synthesis of the precursor of fredericamycin and the facile air oxidation thereof.
Scheme 6: Formal synthesis of fredericamycin A.
Figure 1: Structure of nothapodytine B.
Scheme 7: A useful pyridone synthesis.
Scheme 8: Retrosynthetic logic for nothapodytine B.
Scheme 9: Preparation of a key nothapodytine fragment.
Scheme 10: Total synthesis of nothapodytine B.
Figure 2: Structures of topopyrones.
Scheme 11: Retrosynthetic logic for the linear series of topopyrones.
Scheme 12: Construction of the molecular subunit common to all topopyrones.
Scheme 13: Difficulties encountered during the merger of the topopyrone D moieties.
Scheme 14: Efficient synthesis of a simplified anthraquinone.
Scheme 15: Total synthesis of topopyrone D.
Scheme 16: Total synthesis of topopyrone B.
