title: Enantioselective syntheses of carbocyclic nuleosides 5'-homocarbovir, epi-4'-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations.
abstract: Carbocyclic nucleosides (-)-5'-homocarbovir and (+)-epi-4'-homocarbovir were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. A kinetic enzymatic resolution generated an enantiopure aminocyclopentenol and Pd(0)-mediated decarboxylative allylations of allyl 2,2,2-trifluoroethyl malonates were used to install the 4'-hydroxyethyl groups. Late stage derivatization gave access to the cyclopropylamine congenors, (-)-5'-homoabacavir and (+)-epi-4'-homoabacavir. All carbonucleoside target molecules were evaluated for antiviral activity.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
authors.forename: Lawrence P
authors.initials: LP
authors.lastname: Tardibono
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
authors.forename: Jan
authors.initials: J
authors.lastname: Balzarini