4.8 Article

Synthetic Studies on Daphnicyclidin A: Enantiocontrolled Construction of the BCD Ring System

Journal

ORGANIC LETTERS
Volume 11, Issue 8, Pages 1833-1836

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9003405

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Funding

  1. Grobal COE program for International Center of Research & Education for Molecular Complex Chemistry, Tohoku University

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An enantiocontrolled entry to the tricyclic core of daphnicyclidin A with five chiral centers including an all-carbon quaternary center is reported. The synthesis features a highly diastereoselective conjugate addition of nitromethane, an Ireland-Claisen rearrangement, and a tandem acyliminium/Mannich-type reaction.

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