中华医学超声杂志

应用化学 ›› 2010, Vol. 27 ›› Issue (02): 240-242.DOI: 10.3724/SP.J.1095.2010.90175

• 研究简报 • 上一篇    下一篇

天然海洋环酯肽Stereocalpin A中间体的合成

冯乙巳1,董文杰1,张博1,汤琳1,谭问非2,许华建1*   

  1. (1.合肥工业大学化学工程学院 合肥 230009;2.北京大学深圳研究生院化学基因组学实验室 深圳)
  • 收稿日期:2009-03-13 修回日期:2009-05-19 出版日期:2010-02-10 发布日期:2010-02-10
  • 通讯作者: 许华建,男,博士,教授; E-mail:hjxu@ustc.edu; 研究方向：药物合成
  • 基金资助:
    国家自然科学基金(20802035)深圳市科技计划(SZKJ-2006017)资助项目

Synthesis of the Segment of Natural Cyclic Depsipeptide Stereocalpin A

FENG Yi-Si1, DONG Wen-Jie1, ZHANG Bo1, SHANG Lin1, TAN Wen-Fei2, XU Hua-Jian1*   

  1. (1.School of Chemical Engineering,Hefei University of Technology,Hefei 230009;
    2.Laboratory of Chemical Genomics,Shenzhen Graduate School of Peking University,Shenzhen)
  • Received:2009-03-13 Revised:2009-05-19 Published:2010-02-10 Online:2010-02-10

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摘要：

以D-苯丙氨酸为原料，经过硼氢化钠/碘还原后与三光气在碱性条件下环合得到Evans手性助剂(R)-4-苄基-2-噁唑烷酮(2)，然后将其与丙酰氯缩合，经过LDA偶联、反式Aldol等反应，合成了天然环酯肽Stereocalpin A中含有的独特结构片段，该片段对3种人实体瘤细胞系(HT-29, B16/F10, HepG2)具有中等细胞毒性，总收率为30.6%。结果表明,合成路线简便可行，反应产率高，立体选择性好。 是制备该化合物的有效途径。

关键词: Stereocalpin A，反式Aldol反应，三光气

Abstract:

(R)-4-Benzyl-2-oxazolidinone, an Evans chiral auxiliary reagent, was synthesized from D-phenylalanine as a starting material, which was reduced by sodium borohydride/iodine followed by reacting with bis(trichloromethyl) carbonate under alkaline condition. Then the (R)-4-benzyl-2-oxazolidinone was condensated with propionyl chloride and coupled with LDA. After the antiAldol reaction, a unique segment of Stereocalpin A was obtained in an overall yield of 30.6% which has moderate cytotoxicity against three human solid tumor cell lines(HT-29, B16/F10, HepG2). The developed method is efficient to synthesize this compound with high yield and selectivity.

Key words: stereocalpin A,antiAldol reactions,bis(trichloromethyl) carbonate

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