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A Concise Total Synthesis of (-)-Mesembrine
Wang, Lu-Ning; Cui, Qi; Yu, Zhi-Xiang
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
2016-11-04
DOI10.1021/acs.joc.6b01908
Volume81Issue:21Pages:10165-10171
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS KeywordCATALYZED 5+1 CYCLOADDITION ; DEAROMATIVE CYCLIZATION ; FORMAL SYNTHESIS ; MESEMBRINE ; KETONES ; CO ; VINYLCYCLOPROPANES ; (+)-MESEMBRINE ; SULFONAMIDES ; ALKALOIDS
AbstractA 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.
Language英语
WOS IDWOS:000387303300008
Citation statistics
Cited Times:16[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/150358
Collection中国科学院大连化学物理研究所
AffiliationPeking Univ, Key Lab Bioorgan Chem & Mol Engn, Coll Chem, BNLMS,Minist Educ, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
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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