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题名: A Concise Total Synthesis of (-)-Mesembrine
作者: Wang, Lu-Ning1;  Cui, Qi1;  Yu, Zhi-Xiang1
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2016-11-04
DOI: 10.1021/acs.joc.6b01908
卷: 81, 期:21, 页:10165-10171
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
英文摘要: 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.
关键词[WOS]: CATALYZED 5+1 CYCLOADDITION ;  DEAROMATIVE CYCLIZATION ;  FORMAL SYNTHESIS ;  MESEMBRINE ;  KETONES ;  CO ;  VINYLCYCLOPROPANES ;  (+)-MESEMBRINE ;  SULFONAMIDES ;  ALKALOIDS
语种: 英语
WOS记录号: WOS:000387303300008
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/150358
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Coll Chem, BNLMS,Minist Educ, Beijing 100871, Peoples R China

Recommended Citation:
Wang, Lu-Ning,Cui, Qi,Yu, Zhi-Xiang. A Concise Total Synthesis of (-)-Mesembrine[J]. JOURNAL OF ORGANIC CHEMISTRY,2016,81(21):10165-10171.
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