北京大学医学部机构知识库
Advanced  
IR@PKUHSC  > 北京大学药学院  > 期刊论文
学科主题: 药学
题名:
Total Synthesis of (+)- and (-)-Decursivine and (+/-)-Serotobenine through a Cascade Witkop Photocyclization/Elimination/Addition Sequence: Scope and Mechanistic Insights
作者: Hu, Weimin1; Qin, Hua1; Cui, Yuxin1; Jia, Yanxing1,2
关键词: cascade reactions ; natural products ; photocyclization ; reaction mechanisms ; total synthesis
刊名: CHEMISTRY-A EUROPEAN JOURNAL
发表日期: 2013-02-01
DOI: 10.1002/chem.201204137
卷: 19, 期:9, 页:3139-3147
收录类别: SCI ; IC ; CCR
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
关键词[WOS]: EFFICIENT TOTAL-SYNTHESIS ; ORGANIC-SYNTHESIS ; PHOTOCYCLIZATION REACTIONS ; PHOTOCHEMICAL-SYNTHESIS ; 3,4-BRIDGED INDOLES ; (+/-)-DRAGMACIDIN E ; MICHAEL ADDITION ; RING-CLOSURE ; ATOM ECONOMY ; METHYL-ESTER
英文摘要:

In this article, the total syntheses of antimalarial compound decursivine and its biologically inactive sibling serotobenine are presented. The biomimetic synthesis of (+/-)-serotobenine was investigated first, but failed. During the subsequent investigation of other synthetic routes, we discovered a new cascade Witkop photocyclization/elimination/addition sequence, which enabled the expedient synthesis of not only racemic decursivine and serotobenine, but also enantiopure (+)- and ()-decursivine and a variety of their analogues. The present syntheses represent the shortest pathway for the total synthesis of decursivine and serotobenine to date. Moreover, the newly developed cascade sequence for the total synthesis of decursivine does not need any protecting steps. The scope and the reaction mechanism of the cascade sequence were also studied. A rational mechanism for the cascade sequence is proposed, which is consistent with the previous studies and our current experimental results.

语种: 英语
所属项目编号: 21290180 ; 20972007 ; 20802005 ; 2010CB833200
项目资助者: National Natural Science Foundation of China ; National Basic Research Program of China (973 Program) ; Peking University ; NCET
WOS记录号: WOS:000315142300027
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/60283
Appears in Collections:北京大学药学院_期刊论文

Files in This Item:

There are no files associated with this item.


作者单位: 1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

Recommended Citation:
Hu, Weimin,Qin, Hua,Cui, Yuxin,et al. Total Synthesis of (+)- and (-)-Decursivine and (+/-)-Serotobenine through a Cascade Witkop Photocyclization/Elimination/Addition Sequence: Scope and Mechanistic Insights[J]. CHEMISTRY-A EUROPEAN JOURNAL,2013,19(9):3139-3147.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Google Scholar
Similar articles in Google Scholar
[Hu, Weimin]'s Articles
[Qin, Hua]'s Articles
[Cui, Yuxin]'s Articles
CSDL cross search
Similar articles in CSDL Cross Search
[Hu, Weimin]‘s Articles
[Qin, Hua]‘s Articles
[Cui, Yuxin]‘s Articles
Related Copyright Policies
Null
Social Bookmarking
Add to CiteULike Add to Connotea Add to Del.icio.us Add to Digg Add to Reddit
所有评论 (0)
暂无评论
 
评注功能仅针对注册用户开放,请您登录
您对该条目有什么异议,请填写以下表单,管理员会尽快联系您。
内 容:
Email:  *
单位:
验证码:   刷新
您在IR的使用过程中有什么好的想法或者建议可以反馈给我们。
标 题:
 *
内 容:
Email:  *
验证码:   刷新

Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.

 

 

Valid XHTML 1.0!
Copyright © 2007-2017  北京大学医学部 - Feedback
Powered by CSpace