A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin

被引：45

作者：

Inoue, M

Sasaki, M ^{[1
]}

Tachibana, K

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[2] Japan Sci & Technol Corp, CREST, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 36期

基金：

日本学术振兴会;

关键词：

conformation; medium-ring heterocycles; polyethers; reformatsky reactions;

D O I：

10.1016/S0040-4020(99)00620-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for the construction of the fused hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of gamma-allcoxyallylsilane with acetal to form an O-linked oxacycle and a SmI2-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation was reproduced in the 6-9-6 tricyclic model compound 1 as was observed for that in the ciguatoxin molecule (ring F). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：10949 / 10970

页数：22

共 79 条

[1] USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS [J].