Enantioselective Total Synthesis of (-)-Minovincine in Nine Chemical Steps: An Approach to Ketone Activation in Cascade Catalysis

被引：64

作者：

Laforteza, Brian N. ^{[1
]}

Pickworth, Mark ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 43期

关键词：

alkaloids; enantioselectivity; natural products; organocatalysis; total synthesis; ORGANOCATALYTIC DOMINO REACTIONS; BIOMIMETIC ALKALOID SYNTHESES; DIELS-ALDER REACTION; VINCA ALKALOIDS; MINOVINCINE;

D O I：

10.1002/anie.201305171

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dressed to the nines: The first enantioselective total synthesis of (-)-minovincine has been accomplished in nine chemical steps and 13 % overall yield. A novel, one-step Diels-Alder/β-elimination/conjugate addition organocascade sequence allowed rapid access to the central tetracyclic core in an asymmetric manner. Boc=tert-butoxycarbonyl, LG=leaving group, PMB=para-methoxybenzyl. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11269 / 11272

页数：4

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