Total synthesis of epothilone E and related side-chain modified analogues via a Stille coupling based strategy

被引：76

作者：

Nicolaou, KC

King, NP

Finlay, MRV

He, Y

Roschangar, F

Vourloumis, D

Vallberg, H

Sarabia, F

Ninkovic, S

Hepworth, D

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1999年 / 7卷 / 05期

基金：

美国国家卫生研究院;

关键词：

epothilones; synthesis; Stille coupling; anticancer agents;

D O I：

10.1016/S0968-0896(98)00153-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A Stille coupling strategy has been utilized to complete a total synthesis of epothilone E from vinyl iodide 7 and thiazole stannane 8h. The central core fragment 7 and its trans-isomer 11 were prepared from triene 15 using ring-closing metathesis (RCM), and were subsequently coupled to a variety of alternative stannanes to provide a library of epothilone analogues 18a-o and 19a-o. The Stille coupling approach was then used to prepare epothilone B analogues from the key macrolactone intermediate 24 which was itself synthesized by a macrolactonization based strategy. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：665 / 697

页数：33

共 60 条

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