Stereoselective Syntheses of Tetrahydroesterastin‐β ‐Lactam Analogues

A total synthesis of the optically active tetrahydroesterastin β ‐lactam analogue 2 using Miller's hydroxamate approach is described (Scheme 2). Significant modification of published procedures has resulted in a short and facile stereospecific preparation of the N‐[(benzyloxycarbonyl)methyl]‐β ‐lactam 17 starting from the readily available D‐serine. This material served as intermediate for the preparation of a variety of N‐[(benzyloxycarbonyl)methyl]tetrahydroesterastin β‐lactam analogues (Scheme 5).