15 D-glucoseを出発原料とした海産天然物の合成研究(口頭発表の部)

概要

論文の詳細を見る
There are many reports of the syntheses of natural products using sugars as a starting material. We examined the syntheses of some marine natural products from D-glucose. (1) Total synthesis of bengamide E (1) Bengamide E (1), one of the members of bengamide family, is a novel sponged-derived natural product and has a unique structure. Our synthetic plan is to utilized the entire carbon skeleton of D-glucose for the preparation of the side chain. Inversion of the stereochemistry of the hydroxy groups at C-3 and C-4 was accomplished according to the literature procedure. The formation of the terminal E-olefin by Julia's protocol provided 12, was condensed with cyclo-L-lysine to give 13. Deprotection afforded bengamide E (1). (2) Synthetic studies of ciguatoxin (16) Ciguatoxin (16) is the toxic principle of ciguatera, which is responsive for the most widespread food poisoning of non bacterial origin. In 1989 Yasumoto et al established the whole structure including relative stereochemistry of ciguatoxin (16) and its congener, gambiertoxin 4B (17). In order to open the way to immunoassay of these toxins and to obtain more reliable information on the absolute configuration of these toxins, we planned the preparation of the ABC ring flamework of these toxins.
1993-09-10