Synthesis of novel purinyl-1'-homocarbanucleosides based on a cyclopenta[b]pyrazine system.
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.
Balo
Carmen
C
Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela., Santiago de Compostela, Spain.
López
Carmen
C
Caamaño
Olga
O
Fernández
Franco
F
García-Mera
Xerardo
X
Rodríguez-Borges
José Enrique
JE
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
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