- A concise synthesis of (+)-cerulenin from a chiral oxiranyllithium
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(+)-Cerulenin, a potent fungal inactivator of fatty acid synthases, has been prepared in optically pure form by a sequence involving reaction of a chiral oxiranyllithium with (4E,7E)-nonadienal. Synthesis of the former takes advantage of a particularly favorable Sharpless epoxidation and metalation to a configurationally stable organolithium, while the latter is available in quantity by a direct and improved route.
- Mani, Neelakandha S.,Townsend, Craig A.
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- A convergent asymmetric synthesis of γ-butenolides
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The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded γ-butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of γ-butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin.
- Renard, Marc,Ghosez, Léon A.
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p. 2597 - 2608
(2007/10/03)
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- Synthesis of 4-alkyl-4-alkoxybutenolides having unsaturated side chains via chromium carbene complex photochemistry: (+)-cerulenin
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The photochemical reaction between optically active ene carbamates and chromium alkoxycarbene complexes containing unsaturated aliphatic side chains was further developed. Although remote olefinic groups, including conjugated dienes, were tolerated, a homoallylic side chain underwent intramolecular reaction to give a strained cyclobutanone. (+)-Cerulenin was synthesized utilizing the photochemical reaction of an alkynylcarbene complex with an optically active ene carbamate and the bis(π-crotyl)nickel halide alkylation of a vinyl bromide as key steps.
- Kedar, Tracey E.,Miller, Michael W.,Hegedus, Louis S.
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p. 6121 - 6126
(2007/10/03)
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- Syntheses of cerulenin and its analogs. I. Cerulenin and its analogs with modified side chain
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Optically active cerulenin 1, a potent inhibitor of fatty acid synthetase, was prepared via the condensation of the epoxy aldehyde 8 and the alkenyl lithium 16. In order to evaluate the effects of (E,E)-1,4-double bonds of the cerulenin side chain on the interaction with the enzyme, a series of optically active cerulenin analogs 32a-i with modified side chains and tetrahydrocerulenin 3 were synthesized by similar procedures.
- Morisaki,Funabashi,Furukawa,Shimazawa,Kanematsu,Ando,Okuda,Iwasaki
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p. 2945 - 2953
(2007/10/02)
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- A novel stereoselective synthesis of (+)-cerulenin and (+)-tetrahydrocerulenin
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An antibiotic natural (+)-cerulenin and (+)-tetrahydrocerulenin have been synthesized, based on successive alkylation and reduction of chiral cyclic imide with C2-symmetry derived from D-tartaric acid.
- Yoda,Katagiri,Takabe
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p. 6771 - 6774
(2007/10/02)
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