Synthesis Of 6β-Methoxy-6α-Hydroxymethylpenenms

Article abstract of DOI:10.1016/0040-4020(95)00637-N

6α-Hydroxymethyl-6β-methoxy-2-phenoxymethylpenem was synthesized from benzyl 6β-bromo-6α-methoxypenicillanate via radical addition at 6α-position of methyl tributyltinacrylate and tributyltinstyrene inter alia.The reaction sequence to penem proceeds via secopenicillanates according to established procedures.The good yield of the radical reaction and its stereoselectivity provide a useful entry to the 6α-substituted 6β-methoxypenems and in particular to the 6α-hydroxymethyl-6β-methoxypenems.