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Synthesis of Unsaturated Phosphonates as Acyclic Nucleosides Analogues

Synthesis of the starting allenes began with the coupling of appropriate carbonyl compounds with the acetylenic Grignard compounds to afford propargylic alcohols. Treatment of the propargylic alcohols with diethyl chlorophosphite in the presence of triethylamine afforded, after a [2,3]-sigmatropic rearrangement, allenes in good yields. Condensation of tosylates (1) with adenine in the presence of Cs2CO3 in DMF at 80◦C gave (2) and (3) in ∼50% yields. Structures of (2) and (3) were identified by IR, 1H, 13C, 31P, MS spectral data, and x-ray analysis.