Synthesis of (6R) 4-t-butoxycarbonyl-7-hydroxymethyl-1-oxa-3-cephem from D-arabinal

Article abstract of DOI:10.1016/0040-4020(94)00954-S

Readily available from 3,4-di-O-trimethylsilyl-D-arabinal (13) bicyclic β-lactam 14 was converted into ylide 17 which was subsequently desilylated and subjected to glycolic cleavage of the vic-diol grouping. Dialdehyde 19 spontaneously cyclized to a 1-oxacephem skeleton 16 which was subsequently reduced to t-butyl 7-hydroxymethyl-1-oxa-3-cephem-4-carboxylate (21).