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学科主题: 药学
题名:
Total synthesis of (-)-incarvilline and (-)-incarvillateine
作者: Zhang, Fengying; Jia, Yanxing
刊名: TETRAHEDRON
发表日期: 2009-08-22
DOI: 10.1016/j.tet.2009.06.068
卷: 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
所属项目编号: 20842004 ; 20802005 ; 200800011055
项目资助者: Peking University ; National Science Foundation of China ; Ministry of Education of China
WOS记录号: WOS:000269282400008
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/68087
Appears in Collections:北京大学药学院_期刊论文

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作者单位: Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China

Recommended Citation:
Zhang, Fengying,Jia, Yanxing. Total synthesis of (-)-incarvilline and (-)-incarvillateine[J]. TETRAHEDRON,2009,65(34):6840-6843.
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