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Protecting-Group-Free Enantioselective Synthesis of (-)-Pallavicinin and (+)-Neopallavicinin
Huang, Bin1; Guo, Lei1; Jia, Yanxing1,2
关键词epoxidation natural products palladium terpenoids total synthesis
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2015-11-09
DOI10.1002/anie.201506575
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
资助者National Natural Science Foundation of China ; National Natural Science Foundation of China
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
资助者National Natural Science Foundation of China ; National Natural Science Foundation of China
WOS记录号WOS:000364395100018
Citation statistics
Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/65986
Collection北京大学药学院
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
GB/T 7714
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.
APA Huang, Bin,Guo, Lei,&Jia, Yanxing.(2015).Protecting-Group-Free Enantioselective Synthesis of (-)-Pallavicinin and (+)-Neopallavicinin.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,54(46),13599-13603.
MLA Huang, Bin,et al."Protecting-Group-Free Enantioselective Synthesis of (-)-Pallavicinin and (+)-Neopallavicinin".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54.46(2015):13599-13603.
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