One-pot Diels–Alder cycloaddition/gold(I)-catalyzed 6-endo-dig cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone framework

Beilstein Journal of Organic Chemistry

Gabriel Bellavance¹  Louis Barriault¹  Francis Barabé¹  Boubacar Sow¹ 

[1] Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Canada, K1N 6N5;

关键词: bicyclo[3.3.1]nonenone;    carbocyclization;    Diels–Alder;    gold catalysis;    one-pot process;   

DOI  :  10.3762/bjoc.7.114

来源: DOAJ

【 摘 要 】

The rapid synthesis of bicyclo[m.n.1]alkanone cores possessing quaternary carbon centers adjacent to a bridged ketone represents a significant synthetic challenge. This type of architectural feature is embedded in various complex biologically active compounds such as hyperforin and garsubellin A. Herein, we report a highly diastereoselective one-pot Diels–Alder reaction/Au(I)-catalyzed carbocyclization to generate bicyclo[3.3.1]alkanones in yields ranging from 48–93%.

【 授权许可】

Unknown