Chiral N-heterocyclic carbenes in natural product synthesis: Application of Ru-catalyzed asymmetric ring-opening/cross-metathesis and Cu-catalyzed allylic alkylation to total synthesis of baconipyrone C

被引：130

作者：

Gillingham, Dennis G. ^{[1
]}

Hoveyda, Amir H. ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 21期

关键词：

allylic alkylation; asymmetric catalysis; natural products; N-heterocyclic carbenes; olefin metathesis;

D O I：

10.1002/anie.200700501

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Chiral carbenes as major players: Two recently discovered chiral N-heterocyclic carbene (NHC) complexes play a crucial role in a concise enantioselective total synthesis of baconipyrone C (see scheme). An (NHC)Cu complex catalyzes a double asymmetric allylic alkylation (AAA), and an (NHC)Ru complex catalyzes an asymmetric ring-opening/cross- metathesis (AROM/CM) to establish the absolute configuration of the target. RCM = ring-closing metathesis. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3860 / 3864

页数：5

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