title: Synthesis of 4'-methyl and 4'-cyano carbocyclic 2',3'-didehydro nucleoside analogues via 1,4-addition to substituted cyclopentenones.
abstract: Carbocyclic 4'-methyl and 4'-cyano nucleoside analogues were synthesized using the Michael reaction to introduce the 4'-substituent and Pd-catalyzed allylic substitution to introduce the nucleoside base. Use of both the desired beta- and undesired alpha-1'-carbonate diastereomers in the Pd-catalyzed substitution was demonstrated in principle by epimerization of the alpha-diastereomer and kinetic diastereodifferentiation of a 1:1 alpha/beta mixture of 1'-carbonates.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA. louis.hegedus@colostate.edu
authors.forename: Louis S
authors.initials: LS
authors.lastname: Hegedus
authors.forename: Jeff
authors.initials: J
authors.lastname: Cross
mesh_terms: D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D009705:Nucleosides; C013905:cyclopentenone