A new concept for the preparation of beta-L- and beta-D-2',3'-dideoxynucleoside analogues.
[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.
Albert
Martin
M
Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria. albert@orgc.tu-graz.ac.at
De Souza
Dominic
D
Feiertag
Petra
P
Hönig
Helmut
H
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
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D015224:Dideoxynucleosides