A Concise Total Synthesis of (-)-Mesembrine

被引：41

作者：

Wang, Lu-Ning ^{[1
]}

Cui, Qi ^{[1
]}

Yu, Zhi-Xiang ^{[1
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Coll Chem, BNLMS,Minist Educ, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 21期

关键词：

CATALYZED 5+1 CYCLOADDITION; DEAROMATIVE CYCLIZATION; FORMAL SYNTHESIS; MESEMBRINE; KETONES; CO; VINYLCYCLOPROPANES; (+)-MESEMBRINE; SULFONAMIDES; ALKALOIDS;

D O I：

10.1021/acs.joc.6b01908

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 beta,gamma-cyclohexenone 2c with aryl bromide 5 (using dppe ligand for racemic or (S)-Antphos ligand for asymmetric synthesis) to give gamma,gamma-disubstituted alpha,beta-cyclohexenone 1c. Finally, aza-Michael addition converted 1c to mesembrine.

引用

收藏

页码：10165 / 10171

页数：7

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