Syntheses of Cerulenin and Its Analogs. I. Cerulenin and Its Analogs with Modified Side Chain

Naoko MORISAKI; Hiroshi FUNABASHI; Jun FURUKAWA; Rumiko SHIMAZAWA; Akira KANEMATSU; Toshiaki ANDO; Shigenobu OKUDA; Shigeo IWASAKI

doi:10.1248/cpb.40.2945

Naoko MORISAKI, Hiroshi FUNABASHI, Jun FURUKAWA, Rumiko SHIMAZAWA, Akira KANEMATSU, Toshiaki ANDO, Shigenobu OKUDA, Shigeo IWASAKI

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Keywords: cerulenin, cerulenin analog, fatty acid synthetase inhibitor, synthesis

JOURNAL FREE ACCESS

1992 Volume 40 Issue 11 Pages 2945-2953

DOI https://doi.org/10.1248/cpb.40.2945

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Abstract

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 bounds 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.

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