Sulphenylation and halogenation reactions leading selectively to cis-carbapenem precursors; stereospecific synthesis of (±)-6-epithienamycin
Abstract
Introduction of sulphenyl or halogen substituents at C-7 of ketone (1), followed by stereospecific reduction steps, provides a selective route either to the (6RS,7RS,9RS) or to the (6RS,7RS,9RS) isomers, (10) and (11), of 7-(1-hydroxyethyl)-8-oxo-1-aza-3-oxabicyclo[4.2.0]octane-2-spirocyclohexane.