Formal total synthesis of hemibrevetoxin B by a convergent strategy

被引：31

作者：

Fujiwara, K ^{[1
]}

Sato, D ^{[1
]}

Watanabe, M ^{[1
]}

Morishita, H ^{[1
]}

Murai, A ^{[1
]}

Kawai, H ^{[1
]}

Suzuki, T ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 27期

关键词：

polyether; hemibrevetoxin B; natural product synthesis; acyl anion equivalent; convergent synthesis;

D O I：

10.1016/j.tetlet.2004.05.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Concise construction of the trans-fused 7/7/6/6 tetracyclic ether part of hemibrevetoxin B (1) was achieved by a convergent strategy based on coupling reaction of an acyl anion equivalent, reductive cyclization of an alpha,epsilon-dihydroxyketone, and introduction of a methyl group at the central ring junction by the Nicolaou method. The resultant tetracyclic ether was transformed into the known intermediate, which was already converted to 1 by the Yamamoto group, thereby completing the formal total synthesis of 1. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5243 / 5246

页数：4

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