Synthesis of acyclic bis-vinyl pyrimidines: a general route to d4T via metathesis

DF Ewing, V Glaçon, G Mackenzie, D Postel, C Len

Index: Ewing; Glacon; Mackenzie; Postel; Len Tetrahedron, 2003 , vol. 59, # 7 p. 941 - 945

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Citation Number: 18

Abstract

Unsaturated acyclic pyrimidine analogues, 1-{1-[1-(hydroxymethyl) prop-2-enyloxy] prop-2- enyl} uracil, 1-{1-[1-(hydroxymethyl) prop-2-enyloxy] prop-2-enyl} thymine and 1-{1-[1- (hydroxymethyl) prop-2-enyloxy] prop-2-enyl} cytosine having two asymmetric carbon atoms have been prepared in good yield starting from uridine and 5-methyluridine. The bis-vinyl thymine derivative underwent ring closure metathesis to give d4T, thus providing a novel ...