title: Synthesis of novel purinyl-1'-homocarbanucleosides based on a cyclopenta[b]pyrazine system.
abstract: cis-2,3-Diphenyl-6,7-dihydro-5H-cyclopenta[b]pyrazine-5,7-dimethanol, prepared by Diels-Alder reaction from cyclopentadiene and appropriately protected 2-imidazolone--followed by dihydroxylation, glycol protection, diamine deprotection, condensation with benzyl, glycol deprotection, oxidative cleavage and reduction--, was used to synthesize (+/-)-cis-([7-(6-chloro-9H-purin-9-yl)methyl]-2,3-diphenyl-6,7-dihydro-5H-cyclopenta[b]pyrazin-5-yl)methanol, a key intermediate for novel 1'-homocarbanucleosides based on a cyclopenta[b]pyrazine scaffold as shown by its conversion into several 6-substituted purinyl derivatives.
authors.affiliation: Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela., Santiago de Compostela, Spain.
authors.forename: Carmen
authors.initials: C
authors.lastname: Balo
authors.forename: Carmen
authors.initials: C
authors.lastname: López
authors.forename: Olga
authors.initials: O
authors.lastname: Caamaño
authors.forename: Franco
authors.initials: F
authors.lastname: Fernández
authors.forename: Xerardo
authors.initials: X
authors.lastname: García-Mera
authors.forename: José Enrique
authors.initials: JE
authors.lastname: Rodríguez-Borges
mesh_terms: D018360:Crystallography, X-Ray; D006900:Hydroxylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010084:Oxidation-Reduction; D011687:Purines; D011719:Pyrazines / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D011687:Purines; D011719:Pyrazines; C529688:cis-((7-(6-chloro-9H-purin-9-yl)methyl)-2,3-diphenyl-6,7-dihydro-5H-cyclopenta(b)pyrazin-5-yl)methanol; C529687:cis-2,3-diphenyl-6,7-dihydro-5H-cyclopenta(b)pyrazine-5,7-dimethanol