Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

被引：36

作者：

Kobayashi, S ^{[1
]}

Takahashi, Y ^{[1
]}

Komano, K ^{[1
]}

Alizadeh, BH ^{[1
]}

Kawada, Y ^{[1
]}

Oishi, T ^{[1
]}

Tanaka, S ^{[1
]}

Ogasawara, Y ^{[1
]}

Sasaki, S ^{[1
]}

Hirama, M ^{[1
]}

机构：

[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 38期

基金：

日本学术振兴会;

关键词：

asymmetric alkylation; asymmetric aldol condensation; ring-closing metathesis; ciguatoxin; CTX3C;

D O I：

10.1016/j.tet.2004.07.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8375 / 8396

页数：22

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