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Short Paper | Special issue | Vol 99, No. 2, 2019, pp.1388-1397
Published online, 25th February, 2019
DOI: 10.3987/COM-18-S(F)83
Study toward an Asymmetric and Catalytic Synthesis of Koumine

David Reyes Loya, Jacques Maddaluno, and Michaël De Paolis*

*Normandie Université, UNIROUEN, INSA de Rouen, CNRS, Laboratoire COBRA (UMR 6014 & FR 3038), 76000 Rouen, France

Abstract

A synthetic study of koumine, a natural product with a densely functionalized and inspiring heterocyclic skeleton, was conducted by exploring a strategy of desymmetrization of 1,3-cyclohexanedione by an intramolecular vinylation reaction of an enolate under palladium catalysis to give a strained bridgehead 1,3-cyclohexanedione scaffold. In the course of the study, a domino ring expansion was discovered and developed.