Synthesis and conformational analysis of new cyclobutane-fused nucleosides |
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Authors: | Alibés Ramon Alvárez-Larena Angel de March Pedro Figueredo Marta Font Josep Parella Teodor Rustullet Albert |
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Affiliation: | Universitat Autonoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain. ramon.alibes@uab.es |
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Abstract: | [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. |
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