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Tetrahedron

Publication date: 2011-02-01
Volume: 67 Pages: 825 - 829
Publisher: Pergamon Press

Author:

Tardibono, Lawrence P
Miller, Marvin J ; Balzarini, Jan

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, ANTIVIRAL ACTIVITY, POLYOXIN-C, ABACAVIR, AMINOCYCLOPENTENOLS, SUBSTRATE, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3101 Biochemistry and cell biology, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

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.