Approaches to the Synthesis of Sinefungin Via Nitroaldol Reactions

Abstract

The nucleoside antibiotic sinefungin (1) and its 6′-epimer have been synthesised by a reaction sequence involving as a key step the nitro-aldol reaction between N^b-benzoyl-2′, 3′-O-isopropylideneadenosine-5′-aldehyde (12) and diphenylmethyl-N-t-butyloxycarbonyl-σ-nitro-L-norvaline (11), catalysed by tetrabutylammonium fluoride.