Preparation of 8-oxo-7-(1-hydroxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane derivatives: intermediates for thienamycin synthesis

Abstract

Readily available tetrahydro-1,3-oxazines on acylation with diketen followed by diazo exchange, irradiation, and reduction give 8-oxo-7-(1-hydroxyethyl)-3-oxa-l-azabicyclo[4.2.0]octane derivatives having trans-substituents about the β-lactam ring.