Département de chimie moléculaire

The stereoselective synthesis of penmacric acid, an optically active C-4 substituted pyroglutamic acid, has been efficiently achieved through an unusual 11-step sequence starting from simple N-triisopropylsilylpyrrole. The key steps are the initial addn. of the N-triisopropylsilylpyrrole onto a chiral nitrone, reductive hydrogenation of the pyrrole ring, followed by oxidn. of the corresponding pyrrolidine into pyrrolidinone to the desired pyroglutamic acid moiety. [on SciFinder(R)]