Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin

被引：47

作者：

Asai, M ^{[1
]}

Nishikawa, T ^{[1
]}

Ohyabu, N ^{[1
]}

Yamamoto, N ^{[1
]}

Isobe, M ^{[1
]}

机构：

[1] Nagoya Univ, Sch Bioagr Sci, Organ Chem Lab, Nagoya, Aichi 4648601, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 21期

基金：

日本学术振兴会;

关键词：

tetrodotoxin; guanidine; asymmetric synthesis; marine metabolites;

D O I：

10.1016/S0040-4020(01)00382-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of (-)-5,1 1-dideoxytetrodotoxin, an analog of puffer fish toxin, was accomplished from a common key intermediate through a novel hydroxylation at the C-8 position with neighboring group participation of trichloroacetamide, a highly stereoselective addition of acetylide as an equivalent of carboxylic acid, and a new guanidine synthesis from trichloroacetamide as key steps. This study presents the first asymmetric synthesis among tetrodotoxin and its analogs. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4543 / 4558

页数：16

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