jo6b01908_si_001.pdf (1.19 MB)
A Concise Total Synthesis of (−)-Mesembrine
journal contribution
posted on 2016-10-10, 00:00 authored by Lu-Ning Wang, Qi Cui, Zhi-Xiang YuA concise
total synthesis of mesembrine (four steps from known compound) was
achieved both racemically and asymmetrically. Two key reactions were
used here. One is the Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropane 3c and CO. The other one is Buchwald’s Pd-catalyzed
coupling reaction that coupled β,γ-cyclohexenone 2c with aryl bromide 5 (using dppe ligand for
racemic or (S)-Antphos ligand for asymmetric synthesis)
to give γ,γ-disubstituted α,β-cyclohexenone 1c. Finally, aza-Michael addition converted 1c to mesembrine.