Asymmetric synthesis of cyclohexene nucleoside analogues
Sylvain Dalençon1, Ramzi Aït Youcef, Muriel Pipelier
1UCO2M, UMR CNRS 6011, Faculté de Sciences et Techniques, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
Abstract:
The asymmetric synthesis of novel cyclohexene nucleoside analogues 12 and 15 is described. An enantiospecific Diels-Alder reaction between (E,E)-diene 2 and (+)-5-(d-mentyloxy)-2(5H)-furanone 3 provided the cycloadduct isomer 4. Three additional steps yielded amine 8 allowing the constructions of the thymine and adenine moieties to afford intermediates 11 and 14, respectively. Amination or cyclization and removal of the protecting groups occurred in one step in the presence of ammonia, giving the target six-membered ring nucleosides.
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