SYNTHESIS OF HOMOCHIRAL 4-AMINO-4-CARBOXY-2-PHOSPHONOMETHYLPYRROLIDINES VIA A DIASTEREOSELECTIVE BUCHERER-BERGS REACTION OF 4-OXOPYRROLIDINE DERIVATIVE - NOVEL CONFORMATIONALLY RESTRICTED AP-5 ANALOGS

Asymmetric synthesis of 4-amino-4-carboxy-2-phosphonomethylpyrrolidine s 1 and 2, which can be viewed as novel conformationally restricted an alogues of 2-amino-5-phosphonopentanoic acid (AP 5) incorporated into the pyrrolidine ring, was achieved from trans-4-hydroxy-L-proline as a homochiral starting material using the diastereoselective Bucherer-Be rgs reaction 2-[(diisopropylphosphonyl)methyl]-4-oxopyrrolidine 12.