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
收藏
页码：11269 / 11272
页数：4
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