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Total Synthesis of Clavicipitic Acid and Aurantioclavine: Stereochemistry of Clavicipitic Acid Revisited
Xu, Zhengren1; Hu, Weimin1; Liu, Qiang1; Zhang, Lihe1; Jia, Yanxing1,2
刊名JOURNAL OF ORGANIC CHEMISTRY
2010-11-19
DOI10.1021/jo101506c
75期:22页:7626-7635
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 ; National Natural Science Foundation of China ; National Basic Research Program of China ; Peking University ; National Natural Science Foundation of China ; National Basic Research Program of China
研究领域[WOS]Chemistry
关键词[WOS]PALLADIUM-CATALYZED REACTIONS ; ALPHA-AMINO-ACIDS ; EFFICIENT TOTAL-SYNTHESIS ; SUZUKI-MIYAURA REACTION ; C-H ACTIVATION ; 4-SUBSTITUTED INDOLES ; ERGOT ALKALOIDS ; ENANTIOSELECTIVE SYNTHESIS ; SECONDARY ALCOHOLS ; (-)-CIS-CLAVICIPITIC ACID
英文摘要

The stereocontrolled total synthesis of clavicipitic acid and aurantioclavine from a common azepino[5,4,3-cd]-indole intermediate is reported This key azepinoindole nucleus was constructed via a one-pot Heck/Boc-deprotection/aminocyclization process from the 4-iodotryptophan derivative, which was assembled by a Pd-catalyzed indole synthesis procedure After two or three additional deprotection steps from the azepinoindole intermediates, (-)-trans- and (-)-cis-clavicipitic acid were prepared The syntheses of both (-)- and (+)-aurantioclavine were achieved with the same azepinoindole intermediates utilizing the Barton decarboxylation reaction as the key step to remove the stereohindered carboxylic acid During the course of our synthesis, mis-assigned configurations of the synthesized clavicipitic acids and their derivatives in the literature were identified Extensive studies including 2D-NMR study, X-ray diffraction analysis, titration experiment, and R(f) value comparison unambiguously confirmed the new configuration assignment The trans and cis configuration assignments of the synthesized clavicipitic acids and their derivatives in the past literature should be switched

语种英语
所属项目编号20802005 ; 20972007 ; 2010CB833200
资助者Peking University ; National Natural Science Foundation of China ; National Basic Research Program of China ; Peking University ; National Natural Science Foundation of China ; National Basic Research Program of China
WOS记录号WOS:000284080300015
Citation statistics
Cited Times:48[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/400002259/53801
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.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
Recommended Citation
GB/T 7714
Xu, Zhengren,Hu, Weimin,Liu, Qiang,et al. Total Synthesis of Clavicipitic Acid and Aurantioclavine: Stereochemistry of Clavicipitic Acid Revisited[J]. JOURNAL OF ORGANIC CHEMISTRY,2010,75(22):7626-7635.
APA Xu, Zhengren,Hu, Weimin,Liu, Qiang,Zhang, Lihe,&Jia, Yanxing.(2010).Total Synthesis of Clavicipitic Acid and Aurantioclavine: Stereochemistry of Clavicipitic Acid Revisited.JOURNAL OF ORGANIC CHEMISTRY,75(22),7626-7635.
MLA Xu, Zhengren,et al."Total Synthesis of Clavicipitic Acid and Aurantioclavine: Stereochemistry of Clavicipitic Acid Revisited".JOURNAL OF ORGANIC CHEMISTRY 75.22(2010):7626-7635.
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