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

Add time:08/20/2019    Source:sciencedirect.com

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.

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