title: A new concept for the preparation of beta-L- and beta-D-2',3'-dideoxynucleoside analogues.
abstract: [reaction: see text] A new method for the synthesis of 2',3'-dideoxynucleoside analogues has been developed. An electrochemical activation of 2-substituted furans is followed by the coupling with a pyrimidine or purine base. This gives planar furyl nucleosides as key intermediates, which are hydrogenated cis-selectively to give the corresponding beta-2',3'-dideoxynucleosides as racemic mixtures. An enzymatic kinetic resolution gives rise to beta-D- and beta-L-configured derivatives in high optical purity. This is exemplified by the synthesis of beta-D- and beta-L-3'-deoxythymidine.
authors.affiliation: Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria. albert@orgc.tu-graz.ac.at
authors.forename: Martin
authors.initials: M
authors.lastname: Albert
authors.forename: Dominic
authors.initials: D
authors.lastname: De Souza
authors.forename: Petra
authors.initials: P
authors.lastname: Feiertag
authors.forename: Helmut
authors.initials: H
authors.lastname: Hönig
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D019380:Anti-HIV Agents; D000998:Antiviral Agents; D015224:Dideoxynucleosides