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A Concise Total Synthesis of (-)-Mesembrine
Wang, Lu-Ning; Cui, Qi; Yu, Zhi-Xiang
刊名JOURNAL OF ORGANIC CHEMISTRY
2016-11-04
DOI10.1021/acs.joc.6b01908
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
关键词[WOS]CATALYZED 5+1 CYCLOADDITION ; DEAROMATIVE CYCLIZATION ; FORMAL SYNTHESIS ; MESEMBRINE ; KETONES ; CO ; VINYLCYCLOPROPANES ; (+)-MESEMBRINE ; SULFONAMIDES ; ALKALOIDS
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.
语种英语
WOS记录号WOS:000387303300008
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文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/150358
专题中国科学院大连化学物理研究所
作者单位Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Coll Chem, BNLMS,Minist Educ, Beijing 100871, Peoples R China
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Wang, Lu-Ning,Cui, Qi,Yu, Zhi-Xiang. A Concise Total Synthesis of (-)-Mesembrine[J]. JOURNAL OF ORGANIC CHEMISTRY,2016,81(21):10165-10171.
APA Wang, Lu-Ning,Cui, Qi,&Yu, Zhi-Xiang.(2016).A Concise Total Synthesis of (-)-Mesembrine.JOURNAL OF ORGANIC CHEMISTRY,81(21),10165-10171.
MLA Wang, Lu-Ning,et al."A Concise Total Synthesis of (-)-Mesembrine".JOURNAL OF ORGANIC CHEMISTRY 81.21(2016):10165-10171.
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