Simple and Condensed β-Lactams. Part 28.1 The Synthesis of C-Methylcarumonams and of a Related Bis(carbamate)

Abstract

Racemic carumonam analogues 2a–d are synthesised and found to be devoid of any bacterial activity; NaBH ₄ reduction of 18 affords both epimers of 8c with the (3RS,4RS)-4-[(1RS)] epimer as the main product, and cyclocondensation of phthalimidoacetyl chloride with racemic imine 14 gives rise to the formation of (3RS,4RS)-4-[(1RS)]-15 as a single epimer.