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

Article abstract of DOI:10.1016/S0040-4039(98)02494-0

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 chiral cyclopropane 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. Estexification between fatty acid segments and amide segment with DCC/DMAP and subsequent oxidative deprotection of the MPM group with CAN gave cepaciamides.