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Study on fungitoxic 3-amino-2-piperidinone-containing lipids: Total syntheses of cepaciamides A and B

✍ Scribed by Hiroaki Toshima; Kazuko Maru; Masatoshi Saito; Akitami Ichihara

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
285 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Total syntheses of cepaciamides A and B were accomplished. In the preparation of two fatty acid segments, (S)-malic acid was used as a chiral source to introduce (2S)-configuration. A known ehiral cydopropane derivative was introduced in the segment of cepaciamide A. The formation of (Z)-olefin in the segment of cepaciamide B was achieved by means of partial reduction of the acetylenic bond. Esterification between fatty acid segments and amide segment with DCC/DMAP and subsequent oxidative deprotection of the MPM group with CAN gave cepaciamides.

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