Synthesis and conformational analysis of new cyclobutane-fused nucleosides

Ramon Alibés, Angel Alvárez-Larena, Pedro De March, Marta Figueredo, Josep Font, Teodor Parella, Albert Rustullet

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Abstract

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. © 2006 American Chemical Society.
Original languageEnglish
Pages (from-to)491-494
JournalOrganic Letters
Volume8
Issue number3
DOIs
Publication statusPublished - 2 Feb 2006

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    Alibés, R., Alvárez-Larena, A., De March, P., Figueredo, M., Font, J., Parella, T., & Rustullet, A. (2006). Synthesis and conformational analysis of new cyclobutane-fused nucleosides. Organic Letters, 8(3), 491-494. https://doi.org/10.1021/ol052794y