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Upstream product

• 180153-10-0 (1R,4S,5S)-4-Ethoxy-4-((3E,6E)-octa-3,6-dienyl)-3,6-dioxa-bicyclo[3.1.0]hexan-2-one 
• 72301-02-1 (2R,3R)-3-[(1R,4E,7E)-1-hydroxy-4,7-nonadienyl]-2-oxiranecarboxamide 
• 180153-04-2 (S)-3-[(2S,3S)-2-Ethoxy-5-oxo-2-(4-triisopropylsilanyl-but-3-ynyl)-tetrahydro-furan-3-yl]-4-phenyl-oxazolidin-2-one 
• 180153-07-5 3-((S)-2-Ethoxy-5-oxo-2,5-dihydro-furan-2-yl)-propionaldehyde 
• 180153-05-3 (S)-5-But-3-ynyl-5-ethoxy-5H-furan-2-one 
• 180153-06-4 (S)-5-But-3-enyl-5-ethoxy-5H-furan-2-one 
• 139407-04-8 (2R,3R,4S)-2,3-epoxy-4-hydroxy-7,10-(E,E)-dodecadienamide 
• 180153-09-7 (S)-5-Ethoxy-5-((3E,6E)-octa-3,6-dienyl)-5H-furan-2-one 
• 180153-08-6 (S)-5-Ethoxy-5-((E)-4-iodo-but-3-enyl)-5H-furan-2-one 

Relevant academic research and scientific papers

A convergent asymmetric synthesis of γ-butenolides

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.

A concise synthesis of (+)-cerulenin from a chiral oxiranyllithium

(+)-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.

Synthesis of 4-alkyl-4-alkoxybutenolides having unsaturated side chains via chromium carbene complex photochemistry: (+)-cerulenin

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.

Syntheses of cerulenin and its analogs. I. Cerulenin and its analogs with modified side chain

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.

A novel stereoselective synthesis of (+)-cerulenin and (+)-tetrahydrocerulenin

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.