Synthesis of (S,S)-3-prolylazetidin-2-one: A key component in the synthesis of an HIV gp120 constrained immunogen

Article abstract of DOI:10.1016/0040-4039(95)02340-2

The title compound (2) was synthesized in 5 steps from D-serine. In the absence of protection of the carboxyl group, the β-lactam nucleus underwent a facile rearrangement to provide the undesired diazabicyclo[4.3.0]nonane compound, under acidic or basic c