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Citation: FENG Yi-Si, DONG Wen-Jie, ZHANG Bo, TANG Lin, TAN Wen-Fei, XU Hua-Jian. Synthesis of a Segment of Natural Cyclic Depsipeptide Stereocalpin A[J]. Chinese Journal of Applied Chemistry, ;2010, 27(2): 240-242. doi: 10.3724/SP.J.1095.2010.90175 shu

Synthesis of a Segment of Natural Cyclic Depsipeptide Stereocalpin A

a. School of Chemical Engineering, Hefei University of Technology, Hefei 230009;
b. Laboratory of Chemical Genomics, Shenzhen Graduate School of Peking University, Shenzhen

Received Date: 13 March 2009
Revised Date: 28 July 2009

(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 lithium diisopropylamide(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.
- stereocalpin A,
- anti-Aldol reactions,
- bis(trichloromethyl)carbonate
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