Total syntheses of cepaciamides A and B, novel fungitoxic 3-amino-2- piperidinone-containing lipids produced by Pseudomonas cepacia D-202

Article abstract of DOI:10.1016/S0040-4020(99)00248-3

Total syntheses of cepaciamides A and B were accomplished. (R)-3-Amino- 2-piperidinone was obtained via cyclization of (R)-ornithine. The common amide-linked fatty acid was synthesized via Sharpless AD as the key step. Amide-formation was achieved with DEPC. In the preparation of two fatty acid segments, (S)-malic acid was used as the 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. Esterification between the fatty acid-segments and the amide-segment with DCC/DMAP and subsequent oxidative deprotection of the MPM group with CAN gave cepaciamides.