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Stereocontrolled and Efficient Total Synthesis of (-)-Stephanotic Acid Methyl Ester and (-)-Celogentin C
Hu, Weimin; Zhang, Fengying; Xu, Zhengren; Liu, Qiang; Cui, Yuxin; Jia, Yanxing1
刊名ORGANIC LETTERS
2010-03-05
DOI10.1021/ol902944f
12期:5页:956-959
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
资助者Peking University ; State Key Laboratory of Drug Research ; National Natural Science Foundation of China ; National Basic Research Program of China ; Peking University ; State Key Laboratory of Drug Research ; National Natural Science Foundation of China ; National Basic Research Program of China
研究领域[WOS]Chemistry
关键词[WOS]ANTIMITOTIC BICYCLIC PEPTIDES ; CENTRAL TRYPTOPHAN RESIDUE ; SUZUKI-MIYAURA REACTION ; CELOGENTIN-C ; CELOSIA-ARGENTEA ; ASYMMETRIC-SYNTHESIS ; STEPHANOTIC ACID ; AMINO-ACIDS ; LAPORTEA-MOROIDES ; ORGANIC-SYNTHESIS
英文摘要

A highly stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C was accomplished in longest linear 14 steps (4.6% overall yield) and in 20 steps (1.6% overall yield) from L-tryptophan, respectively. Highlights of the synthesis include a tandem asymmetric Michael addition/bromination/azidation strategy for a ready access to the leucine-tryptophan moiety (Leu-Trp linkage) and an oxidative coupling reaction to form the indole-imidazole linkage.

语种英语
所属项目编号20972007 ; 20802005 ; 2010CB833200
资助者Peking University ; State Key Laboratory of Drug Research ; National Natural Science Foundation of China ; National Basic Research Program of China ; Peking University ; State Key Laboratory of Drug Research ; National Natural Science Foundation of China ; National Basic Research Program of China
WOS记录号WOS:000274841800016
引用统计
被引频次:32[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/400002259/66343
专题北京大学药学院
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 Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
3.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
推荐引用方式
GB/T 7714
Hu, Weimin,Zhang, Fengying,Xu, Zhengren,et al. Stereocontrolled and Efficient Total Synthesis of (-)-Stephanotic Acid Methyl Ester and (-)-Celogentin C[J]. ORGANIC LETTERS,2010,12(5):956-959.
APA Hu, Weimin,Zhang, Fengying,Xu, Zhengren,Liu, Qiang,Cui, Yuxin,&Jia, Yanxing.(2010).Stereocontrolled and Efficient Total Synthesis of (-)-Stephanotic Acid Methyl Ester and (-)-Celogentin C.ORGANIC LETTERS,12(5),956-959.
MLA Hu, Weimin,et al."Stereocontrolled and Efficient Total Synthesis of (-)-Stephanotic Acid Methyl Ester and (-)-Celogentin C".ORGANIC LETTERS 12.5(2010):956-959.
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