P-48 スフィンゴシン由来の機能性脂質の合成(ポスター発表の部)

概要

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We have studied the syntheses of bioactive lipids using natural chiral sources as starting materials. Hayashi et al. isolated a new ceramide digalactoside 1 as a main glycosphingolipid from the marine sponge Halichondria japonica. Penaresidin A 2 and B 3 were isolated as potent actomyosin ATPase activators from Okinawan marine sponge Penares sp. by Kobayashi et al. Here we describe synthetic studies of the ceramide part of I and the straight chain analog of 2. Synthesis of the ceramide part of 1. A partially protected ceramide part 20 of cerebroside 1 has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined. The key step in the synthesis include the regioselective ring opening of chiral epoxide 7 with 2-alkyl-2-lithio-1,3-dithiane and the introduction of hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality. Synthesis of the straight chain analog of 2. The strategy for the construction of azetidine skeleton was a biogenetic-like intramolecular cyclization of a phytosphingosine analog 26, which, in turn, derived from xylose.
天然有機化合物討論会の論文
1994-09-20