Tetrahedron p. 10723 - 10730 (1995)
Update date:2022-09-26
Topics:
Sadeghpour, Bahman M.
Pellicciari, Roberto
Marchioro, Carla
Rossi, Tino
Tamburini, Bruno
et al.
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.
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