Synthetic studies on daphnicyclidin A: enantiocontrolled construction of the BCD ring system.
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.
Ikeda
Shuhei
S
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan.
Shibuya
Masatoshi
M
Kanoh
Naoki
N
Iwabuchi
Yoshiharu
Y