Article Dans Une Revue Journal of Organic Chemistry Année : 2011

Asymmetric Synthesis of Cyclohexene Nucleoside Analogues

Résumé

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.

Domaines

Fichier non déposé

Dates et versions

hal-00661226 , version 1 (18-01-2012)

Identifiants

Citer

Sylvain Dalençon, Ramzi Ait Youcef, Muriel Pipelier, Vincent Maisonneuve, Didier Dubreuil, et al.. Asymmetric Synthesis of Cyclohexene Nucleoside Analogues. Journal of Organic Chemistry, 2011, 76 (19), pp.8059-8063. ⟨10.1021/jo2012708⟩. ⟨hal-00661226⟩
113 Consultations
0 Téléchargements

Altmetric

Partager

  • More