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
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
收藏
页码:4543 / 4558
页数:16
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