TOTAL SYNTHESIS OF A THYMIDINE 2-DEOXYPOLYOXIN-C ANALOG

The synthesis of the thymidine 2-deoxypolyoxin C analogue 10 from a no ncarbohydrate precursor was achieved in 10 steps and 9% yield starting from a chiral gamma,delta-epoxy-beta-hydroxy ester 11 readily availab le from cis-2-butene-1,4-diol, The main steps concern the stereo-and r egioselective opening of the epoxide ring by an azide anion, the stere oselective introduction of the thymine base, and the transformation of the primary alcohol to the acid functionality of the final product. T wo other approaches have also been investigated.