Synthesis and conformational analysis of new cyclobutane-fused nucleosides.
[structure: see text]. A stereselective synthesis of 3-oxabicyclo[3.2.0]heptane nucleoside analogues, which were designed as conformational mimics of the anti-HIV agents 2',3'-didehydro-2',3'-dideoxythimidine (stavudine, d4T) and 2',3'-didehydro-2',3'-dideoxyadenosine (d4A), is described. The target compounds were prepared by condensation of a common intermediate bicyclic acetate, derived from a homochiral 2(5H)-furanone, with pyrimidine and purine bases under modified Vorbrüggen conditions. The conformational behavior of the synthesized nucleoside analogues was studied by NMR spectroscopy and X-ray crystallography.
Alibés
Ramon
R
Universitat Autonoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain. ramon.alibes@uab.es
Alvárez-Larena
Angel
A
de March
Pedro
P
Figueredo
Marta
M
Font
Josep
J
Parella
Teodor
T
Rustullet
Albert
A
D019380:Anti-HIV Agents / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D018119:Stavudine / Q000737:chemistry* / Q000494:pharmacology
D019380:Anti-HIV Agents; D003503:Cyclobutanes; D009705:Nucleosides; D018119:Stavudine