Synthesis of purine nucleosides built on a 3-oxabicyclo[3.2.0]heptane scaffold

Ramon Flores, Albert Rustullet, Ramon Alibés, Angel Álvarez-Larena, Pedro De March, Marta Figueredo, Josep Font

Research output: Contribution to journalArticleResearchpeer-review

29 Citations (Scopus)


The photochemical [2 + 2] cycloaddition of chiral 3-chloro and 3-fluoro-5-hydroxymethyl-2(5H)-furanone to ethylene and acetylene has been studied. The effect of the halogen atom on the chemical yield and facial diastereoselectivity of the cycloaddition process has been evaluated. From the major anti cycloadducts, practical syntheses of several purine cyclobutane and cyclobutene-fused nucleosides containing a halogen atom have been developed. The anti-HIV activity of the new nucleoside analogues has been evaluated. © 2011 American Chemical Society.
Original languageEnglish
Pages (from-to)5369-5383
JournalJournal of Organic Chemistry
Issue number13
Publication statusPublished - 1 Jul 2011


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