Absolute structure of panaxytriol

被引：9

作者：

Satoh, M

Ishii, M

Watanabe, M

Isobe, K

Uchiyama, T

Fujimoto, Y

机构：

[1] Showa Coll Pharmaceut Sci, Machida, Tokyo 1948543, Japan

[2] Nihon Univ, Coll Pharm, Funabashi, Chiba 2748555, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2002年 / 50卷 / 01期

关键词：

panaxytriol; panax species; polyacetylene; absolute configuration; enzyme mediated-acetylation;

D O I：

10.1248/cpb.50.126

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Diastereomeric mixture at C-3 of (9R,10R)-panaxytriol acetonide (3) and (9S,10S)-panaxytriol acetonide (4) were enantioselectively acetylated to give (3R)-acetates (3a-Ac, 4a-Ac) and (3S)-alcohols (3b, 4b) by enzyme mediated-acetylation using CHIRAZYME and vinyl acetate, respectively. Hydrolysis of (3R)-acetate (3a-Ac, 4a-Ac) with CHIRAZYME and phosphate buffer afforded (3R)-alcohols (3a, 4a), respectively. Deprotection of panaxytriol acetonides (3a,3b, 4a,4b) gave panaxatriol and its isomers, respectively, Comparison of optical rotation values of the synthetic panaxatriols with that of the natural one confirmed that the absolute configuration of panaxytriol sould be 3R,9R, 10R.

引用

页码：126 / 128

页数：3

共 8 条

[1] Synthesis of a new type of antitumour agent panaxytriol:synthesis of its four diastereomers [J].