Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge

被引：44

作者：

Kotoku, N ^{[1
]}

Tsujita, H ^{[1
]}

Hiramatsu, A ^{[1
]}

Mori, C ^{[1
]}

Koizumi, N ^{[1
]}

Kobayashi, M ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2005年 / 61卷 / 30期

关键词：

total synthesis; bastadin; oxidative coupling; angiogenesis; marine sponge;

D O I：

10.1016/j.tet.2005.05.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient total synthesis of bastadin 6 (1), a cyclic tetramer of brominated tyrosine derivatives from the marine sponge, lanthella basta, with selective anti-angiogenic activity, was accomplished. We developed a novel Ce(IV)-mediated oxidative coupling reaction of 2,6-dibromophenols to give the diaryl ether derivatives, the characteristic segment of 1. Condensation of two segments and subsequent intramolecular macrocyclization gave bastadin 6 (1) in nine steps, 26% overall yield. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：7211 / 7218

页数：8

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