%0 Journal Article
%A Wang, Lu-Ning
%A Cui, Qi
%A Yu, Zhi-Xiang
%D 2016
%T A Concise Total Synthesis
of (−)-Mesembrine
%U https://acs.figshare.com/articles/journal_contribution/A_Concise_Total_Synthesis_of_-Mesembrine/4138719
%R 10.1021/acs.joc.6b01908.s001
%2 https://ndownloader.figshare.com/files/6757245
%K vinylcyclopropane 3 c
%K Antpho
%K Rh
%K cycloaddition
%K aryl bromide 5
%K racemic
%K Synthesi
%K racemically
%K Buchwald
%K cyclohexenone
%K CO
%K Pd-catalyzed
%K dppe ligand
%K Mesembrine
%K compound
%K aza-Michael addition
%K 1 c
%K Concise
%K disubstituted
%K mesembrine
%K synthesis
%X A 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.
%I ACS Publications