Total Synthesis of a Thymidine 2-Deoxypolyoxin C Analogue.
The synthesis of the thymidine 2-deoxypolyoxin C analogue 10 from a noncarbohydrate precursor was achieved in 10 steps and 9% yield starting from a chiral gamma,delta-epoxy-beta-hydroxy ester 11 readily available from cis-2-butene-1,4-diol. The main steps concern the stereo- and regioselective opening of the epoxide ring by an azide anion, the stereoselective introduction of the thymine base, and the transformation of the primary alcohol to the acid functionality of the final product. Two other approaches have also been investigated.
Dehoux
Cécile
C
Laboratoire de synthèse et physicochimie organique, ESA 5068 associé au CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 4, France.
Fontaine
Evelyne
E
Escudier
Jean-Marc
JM
Baltas
Michel
M
Gorrichon
Liliane
L