%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