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