Organic letters

Synthetic studies on daphnicyclidin A: enantiocontrolled construction of the BCD ring system

S Ikeda, M Shibuya, N Kanoh, Y Iwabuchi

Index: Ikeda, Shuhei; Shibuya, Masatoshi; Kanoh, Naoki; Iwabuchi, Yoshiharu Organic Letters, 2009 , vol. 11, # 8 p. 1833 - 1836

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Citation Number: 42

Abstract

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.