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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (08): 1007-1012. 上一篇    下一篇

研究论文

天然环酯肽Obyanamide的全合成

王晓季*,a，李阳b，陈立功b，郑鹏武a，段学民a，许正双c   

  1. (a江西科技师范学院药学院 南昌 330013)
    (b天津大学化工学院 天津 300072)
    (c北京大学深圳研究生院化学基因实验室 深圳 518055)
  • 收稿日期:2006-08-01 修回日期:1900-01-01 发布日期:2007-07-30
  • 通讯作者: 王晓季*

Total Synthesis of Natural Cyclic Depsipeptide—Obyanamide

WANG Xiao-Ji*,a, LI Yangb, CHEN Li-Gongb, ZHENG Peng-Wua
DUAN Xue-Mina, XU Zheng-Shuangc   

  1. (a School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013)
    (b School of Chemical Engineering, Tianjin University, Tianjin 300072)
    (c Laboratory of Chemical Genomics, The Shenzhen Graduate School of Peking University, Shenzhen 518055)
  • Received:2006-08-01 Revised:1900-01-01 Published:2007-07-30
  • Contact: WANG Xiao-Ji*

PDF

1100

被引次数

5

针对目标化合物Obyanamide的结构特征, 运用反合成设计, 将其切为四个合成片断: N-甲基缬氨酸-N-甲基苯丙氨酸二肽(片断A)、噻唑酸衍生物(片断B)、L-乳酸衍生物(片断C)和β-氨基戊酸衍生物(片断D), 并对各个合成片断进行了合成, 最终顺利完成了对天然海洋环酯肽Obyanamide的全合成. 其化学结构经1H NMR, 13C NMR, HMBC以及HRMS (FAB)予以确证.

关键词: Obyanamide, 全合成, 天然环酯肽

Based on the structural features of obyanamide, the target molecule was disconnected into four fragments by applying retrosynthetic analysis method, i.e., N-Me-Phe-N-Me-Val (fragment A), thiazole carboxy acid derivative (fragment B), lactic acid derivative (fragment C) and unnatural 3-aminopentanoic acid (fragment D). The total synthesis of a natural marine cytotoxic cyclic depsipeptide obyanamide was accomplished successfully from synthesized the fragments A, B, C and D. The structures of the synthesized intermediates and product was identified by 1H NMR, 13C NMR, HMBC and HRMS (FAB) spectra.

Key words: total synthesis, natural cyclic depsipeptide, obyanamide