Synthesis of acyclic bis-vinyl pyrimidines: a general route to d4T via metathesis |
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| Authors: | DF EwingV Glaçon G MackenzieD Postel C Len |
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| Institution: | a Centre for Biological and Organic Chemistry, University of Hull, Hull, HU6 7RX, UK
b Laboratoire des Glucides, Université de Picardie-Jules Verne, 33, rue saint Leu, F-80039 Amiens, France |
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| 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 synthesis of this compound. |
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| Keywords: | d4T bis-vinyl nucleoside double Wittig |
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