Development of organoiron methodology for preparation of the polyene natural product macrolactin A

被引：31

作者：

Bärmann, H ^{[1
]}

Prahlad, V ^{[1
]}

Tao, CL ^{[1
]}

Yun, YK ^{[1
]}

Wang, Z ^{[1
]}

Donaldson, WA ^{[1
]}

机构：

[1] Marquette Univ, Dept Chem, Milwaukee, WI 53201 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 15期

基金：

美国国家卫生研究院;

关键词：

organoiron; macrolactin A; cyclocondensation;

D O I：

10.1016/S0040-4020(99)01111-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methodology for the synthesis of the C7-C13 segment (19) and C14-C24 segment (41) of macrolactin A have been developed. Dicarbonyl(methyl 7-nitro-2E,4Z-heptadienoate)triphenylphosphineiron (19) is prepared by nucleophilic addition to a (1-methoxycarbonylpentadienyl)iron cation. The C23 stereocenter of 41 is established by introduction of a C20 stereocenter, chirality transfer from C20 to C23 followed by (diene)iron mediated selective ionic reduction of the C20 hydroxyl. The C15 stereocenter may be established by nitrile oxide-olefin cyclocondensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：2283 / 2295

页数：13

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