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

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journal contribution
posted on 16.04.2009, 00:00 by Shuhei Ikeda, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi
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.