Enantioselective total synthesis of (+)-cylindricine B
Dallas M Dukes1, Victor K Atanassov1, Joel M Smith1
1Florida State University, Department of Chemistry and Biochemistry, Laboratories of Molecular Recognition 95 Chieftan Way Tallahassee FL 32306 USA jsmith17@fsu.edu.
Abstract:
This article describes the first enantioselective synthesis of the Tasmanian marine alkaloid (+)-cylindricine B. The concise construction of the compound hinged on dearomative retrosynthetic logic combined with a tactical advance in the generation of congested, cyclic, alpha-tertiary amine centers. The scope of this key coupling reaction was explored in addition to providing a synthetic application for Cu-catalyzed enantioselective dearomatization of N-acyl-pyridiniums. The synthesis proceeds in five or six steps from commercially available starting materials.
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