Chinese Journal of Applied Chemistry ›› 2010, Vol. 27 ›› Issue (02): 240-242.DOI: 10.3724/SP.J.1095.2010.90175

• Original Articles • Previous Articles     Next Articles

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


(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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