title: Total Synthesis of a Thymidine 2-Deoxypolyoxin C Analogue.
abstract: 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.
authors.affiliation: Laboratoire de synthèse et physicochimie organique, ESA 5068 associé au CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 4, France.
authors.forename: Cécile
authors.initials: C
authors.lastname: Dehoux
authors.forename: Evelyne
authors.initials: E
authors.lastname: Fontaine
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Escudier
authors.forename: Michel
authors.initials: M
authors.lastname: Baltas
authors.forename: Liliane
authors.initials: L
authors.lastname: Gorrichon