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Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (+/-)-Cephalotaxine
Alternative Title立体选择性亚胺阳离子关环: (+/-)三尖杉碱的高效合成
Liu H(刘浩)1; Yu J(于静)1; Li XY(李新宇)1; Yan R(严睿)1; Xiao JC(肖吉昌)1; Hong R(洪然)1
2015
Source PublicationOrg. Lett.
Volume17Issue:18Pages:4444-4447
AbstractA stereoselective N-iminium ion cyclization with allylsilane to construct vicinal quaternary tertiary carbon centers was developed for the concise synthesis of (+/-)-cephalotaxine. The current strategy features a TiCl4-promoted cyclization and ring-closure metathesis to furnish the spiro-ring system. The stereochemical outcome in the N-acyliminium ion cyclization was rationalized by the stereoelectronic effect of the Z- or E-allylsilane. Two diastereomers arising from the cyclization were merged into the formal synthesis of (+/-)-cephalotaxine.
Subtype论文
Subject Area天然产物有机化学
DOI10.1021/acs.orglett.5b02106
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000361867800012
Citation statistics
Cited Times:19[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39805
Collection中科院天然产物有机化学重点实验室
Corresponding AuthorHong R(洪然)
Affiliation1.中科院上海有机化学研究所, 天然产物有机合成化学重点实验室
2.中科院上海有机化学研究所, 有机氟化学重点实验室
Recommended Citation
GB/T 7714
Liu H,Yu J,Li XY,et al. Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (+/-)-Cephalotaxine[J]. Org. Lett.,2015,17(18):4444-4447.
APA 刘浩,于静,李新宇,严睿,肖吉昌,&洪然.(2015).Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (+/-)-Cephalotaxine.Org. Lett.,17(18),4444-4447.
MLA 刘浩,et al."Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (+/-)-Cephalotaxine".Org. Lett. 17.18(2015):4444-4447.
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