83(P14) セパシアミドAおよびBの全合成(ポスター発表の部)
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Cepaciamides A and B were isolated from Pseudomonas cepacia D-202 as novel fungitoxic 3-amino-2-piperidinone-containing lipids against Botrytis cinerea and Penicillium expansum, which cause the storage rot of beet roots. In order to examine the structure-activity relationship of cepaciamides and their derivatives as biocontrol agents, stereochemically pure compounds must be supplied synthetically due to the difficulty in obtaining a sufficient amount of cepaciamides from Pseudomonas cepacia D-202 because of its low productivity. Furthermore, a large amount of various phospholipids, which occur in close proximity to the very near the cepaciamide fraction, interfere with isolation and purification. Total syntheses of (3R,3'S,2"S,11"S,12"R)-3[3'-(2"-hydroxy-11",12"-methyleneocta-decanoyloxy)hexadecanoylamino]-2-piperidinone (cepaciamide A) and (3R,3'S,2"S,11"Z)-3-[3'-(2"-hydroxy-11"-octadecenoyloxy)hexadecanoylamino]-2-piperidinone (cepaciamide B), were accomplished as described below. (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.
- 天然有機化合物討論会の論文
- 1999-09-01
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