title: Asymmetric synthesis of cyclohexene nucleoside analogues.
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.
authors.affiliation: UCO2M, UMR CNRS 6011, Faculté de Sciences et Techniques, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Dalençon
authors.forename: Ramzi Aït
authors.initials: RA
authors.lastname: Youcef
authors.forename: Muriel
authors.initials: M
authors.lastname: Pipelier
authors.forename: Vincent
authors.initials: V
authors.lastname: Maisonneuve
authors.forename: Didier
authors.initials: D
authors.lastname: Dubreuil
authors.forename: François
authors.initials: F
authors.lastname: Huet
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Legoupy
mesh_terms: D000586:Amination; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D003500:Cyclization; D053138:Cyclohexenes / Q000737:chemistry*; D007536:Isomerism; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D053138:Cyclohexenes; D009705:Nucleosides; C052568:cyclohexene