The title compound was synthesized mainly by palladium catalytic coupling, cyclopropyl ring-opening rearrangement, epoxidation, Swern oxidation, demethanol reactions, and selective reduction. This synthesis was achieved in 16 steps with 9.7% overall yield. Unfortunately, the published spectroscopic data do not match with those of our synthetic compound.

A practical method for the synthesis of lycorine-type alkaloids with cis-B/C ring structure has been developed. Based on the reactions of aminocyclization, palladium-mediated arylation and especially cyclopropyl ring-opening rearrangement, the synthesis of anhydrocaranine, (±)-γ-lycorane and putative (±)-amarbellisine was accomplished.

Total Synthesis of Lycorine-Type Alkaloids by Cyclopropyl Ring-Opening Rearrangement. -Three lycorine-type alkaloids are prepared by a new synthetic method. A newly developed cyclopropyl ring-opening rearrangement allows the practical synthesis of anhydrocaranine (I), racemic -lycorane (II), and putative racemic amarbellisine (III). The structures of the synthesized compounds are confirmed by spectroscopic data. Compound (III) turns out to be a different isomer to the natural amarbellisine. -(LIU, D.; AI, L.; LI, F.; ZHAO, A.; CHEN, J.; ZHANG, H.; LIU*, J.; Org.