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Total synthesis of (-)-incarvilline and (-)-incarvillateine
Zhang, Fengying; Jia, Yanxing
刊名TETRAHEDRON
2009-08-22
DOI10.1016/j.tet.2009.06.068
65期:34页:6840-6843
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]INCARVILLEA-SINENSIS ; ESTERS ; THAPSIGARGINS ; DERIVATIVES ; ANALGESICS ; ALKALOIDS
英文摘要

An enantioselective, concise total synthesis of (-)-incarvilline and (-)-incarvillateine has been achieved in longest linear 9 steps (24.3% overall yield) and in 11 steps (16.5% overall yield) from (-)-carvone, respectively. The present synthesis features a notable Favorskii rearrangement of the O-protected chlorchydrin derivative of (-)-carvone to construct four of the five contiguous stereocenters on the bicyclic piperidine moiety and DMAP-catalyzed esterification of incarvilline with alpha-truxillic acid anhydride to generate incarvillateine skeleton. (C) 2009 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000269282400008
项目编号20842004 ; 20802005 ; 200800011055
资助机构Peking University ; National Science Foundation of China ; Ministry of Education of China
引用统计
被引频次:17[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/68087
专题北京大学药学院
作者单位Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Zhang, Fengying,Jia, Yanxing. Total synthesis of (-)-incarvilline and (-)-incarvillateine[J]. TETRAHEDRON,2009,65(34):6840-6843.
APA Zhang, Fengying,&Jia, Yanxing.(2009).Total synthesis of (-)-incarvilline and (-)-incarvillateine.TETRAHEDRON,65(34),6840-6843.
MLA Zhang, Fengying,et al."Total synthesis of (-)-incarvilline and (-)-incarvillateine".TETRAHEDRON 65.34(2009):6840-6843.
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