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Total synthesis of (-)-indolactam V
Xu, Zhengren1; Zhang, Fengying1; Zhang, Lihe1; Jia, Yanxing1,2
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
2011
DOI10.1039/c0ob01115k
9期:7页:2512-2517
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]DIHYDROTELEOCIDIN-B-4 DIHYDROTELEOCIDIN-B ; LYNGBYATOXIN-A TELEOCIDIN-A-1 ; DIVERSITY-ORIENTED SYNTHESIS ; EFFICIENT TOTAL-SYNTHESIS ; SUZUKI-MIYAURA REACTION ; KINASE-C MODULATORS ; TUMOR PROMOTERS ; TOXIC SUBSTANCE ; BIOLOGICAL EVALUATION ; INDOLACTAM-V
英文摘要

The total synthesis of protein kinase C activator (-)-indolactam V (IL-V) has been successfully completed with two separate approaches: From known 4-nitrotryptophan derivative 3 in 8 steps (49% overall yield) and from L-glutamic acid in 12 steps (18% overall yield), where 4-nitrotryptophanol derivative 4 served as a key intermediate. Derivatives 3 and 4, both incorporating indole 4-substitution and the C-9 stereocenter in IL-V, were synthesized via the Pd-catalyzed indole synthesis from 3-nitro-2-iodoaniline 5 with aldehydes 6 and 7, respectively. Aldehyde 7 was, meanwhile, synthesized from L-glutamic acid in 5 steps (68% yield). Lactamization of the 9-membered ring was achieved using HATU in THF in good yield.

语种英语
WOS记录号WOS:000288456700057
项目编号20802005 ; 20972007 ; 2010CB833200
资助机构National Natural Science Foundation of China ; National Basic Research Program of China (973 Program) ; NCET ; Peking University
引用统计
被引频次:41[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/400002259/66941
专题北京大学药学院
北京大学药学院_药物化学系
北京大学药学院_药学院
作者单位1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
2.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
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Xu, Zhengren,Zhang, Fengying,Zhang, Lihe,et al. Total synthesis of (-)-indolactam V[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2011,9(7):2512-2517.
APA Xu, Zhengren,Zhang, Fengying,Zhang, Lihe,&Jia, Yanxing.(2011).Total synthesis of (-)-indolactam V.ORGANIC & BIOMOLECULAR CHEMISTRY,9(7),2512-2517.
MLA Xu, Zhengren,et al."Total synthesis of (-)-indolactam V".ORGANIC & BIOMOLECULAR CHEMISTRY 9.7(2011):2512-2517.
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