Synthesis of complex 6'-alkynyl-6'-dethia nucleoside analogs of S-adenosylhomocysteine as potential inhibitors of methyltransferases

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The synthesis of complex acetylenic nucleosides containing a 5',6' carbon-carbon bond has been investigated. Two synthetic routes were studies, both starting with an α-substituted butyrolactone, The lactone could be converted to an β-keto sulfone and then to the corresponding enol phosphate diphenyl ester. Reductive elimination to yield the desired aryl acetylene could not be effected without some overreduction to the substituted olefin. Alternatively, the lactone could be converted to an apropriately protected γ-hydroxy aldehyde which was then homologated to a terminal acetylene