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
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
收藏
页码:3860 / 3864
页数:5
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