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学科主题: 药学
题名:
Protecting-Group-Free Enantioselective Synthesis of (-)-Pallavicinin and (+)-Neopallavicinin
作者: Huang, Bin1; Guo, Lei1; Jia, Yanxing1,2
关键词: epoxidation ; natural products ; palladium ; terpenoids ; total synthesis
刊名: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
发表日期: 2015-11-09
DOI: 10.1002/anie.201506575
卷: 54, 期:46, 页:13599-13603
收录类别: SCI
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]: PALLADIUM-CATALYZED CYCLOALKENYLATION ; LIVERWORT PALLAVICINIA-SUBCILIATA ; HOMOALLYL RADICAL REARRANGEMENT ; TERT-BUTYL HYDROPEROXIDE ; DECARBOXYLATIVE ALLYLATION ; NATURAL-PRODUCTS ; EPOXIDATIONS ; ALKALOIDS ; (+/-)-SEROTOBENINE ; ALKYLATION
英文摘要:

The first enantioselective synthesis of (-)-pallavicinin and (+)-neopallavicinin has been achieved in 15 steps. The described synthesis avoids protecting-group manipulations by synthesis designs predicated on highly chemo- and stereoselective transformations. Highlights of the synthesis include a palladium-catalyzed enantioselective decarboxylative allylation to form the chiral all-carbon quaternary stereocenter, a palladium-catalyzed oxidative cyclization to assemble the [3.2.1]-bicyclic moiety, and an unprecedented LiBHEt3-induced fragmentation/protonation of an -hydroxy epoxide to form the -furan ketone with the desired configuration.

语种: 英语
所属项目编号: 21290183 ; 21572008
项目资助者: National Natural Science Foundation of China
WOS记录号: WOS:000364395100018
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/65986
Appears in Collections:北京大学药学院_期刊论文

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作者单位: 1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

Recommended Citation:
Huang, Bin,Guo, Lei,Jia, Yanxing. Protecting-Group-Free Enantioselective Synthesis of (-)-Pallavicinin and (+)-Neopallavicinin[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2015,54(46):13599-13603.
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