学科主题 | 药学 |
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
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2010-11-19 | |
DOI | 10.1021/jo101506c |
卷 | 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 | |
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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