Total synthesis of (±)-manzacidin D

被引：24

作者：

Drouin, C ^{[1
]}

Woo, JCS ^{[1
]}

MacKay, B ^{[1
]}

Lavigne, RMA ^{[1
]}

机构：

[1] Merck Frosst Ctr Therapeut Res, Kirkland, PQ H9H 3L1, Canada

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 39期

基金：

加拿大自然科学与工程研究理事会;

关键词：

manzacidin; iodocyclization; isothiourea; thiourea; formamidine;

D O I：

10.1016/j.tetlet.2004.08.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein the first total synthesis of the alkaloid manzacidin D, in 11 steps and 16% overall yield from commercially available glycine tert-butyl ester hydrochloride. Our synthesis demonstrates for the first time in a total synthesis the utility of two different methodologies. A highly diastereoselective iodocyclization of an olefinic isothiourea is used to induce stereocontrol at the quaternary centre, and to form the heterocyclic core. Conversion of a thiourea to the requisite formamidine is achieved in good yield using our modified procedure. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7197 / 7199

页数：3

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