GABA agonists and uptake inhibitors. Synthesis, absolute stereochemistry, and enantioselectivity of (R)-(-)-and (S)-(+)-homo-. beta.-proline

…, L Brehm, P Krogsgaard-Larsen

Index: Nielsen, Lone; Brehm, Lotte; Krogsgaard-Larsen, Povl Journal of Medicinal Chemistry, 1990 ,  vol. 33,  # 1  p. 71 - 77

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Citation Number: 58

Abstract

Results Synthesis. Conjugate addition of (R)-(+)-1-phenylethylamine to itaconic acid (1) and subsequent cyclization gave a diastereomeric mixture of carboxylic acids 2, which were converted into methyl esters 3 and then separated by preparative HPLC to give 4 and 5 (Scheme I). The purity and stereochemical homogeneity of 4 and 5 were established by TLC analysis and by GC/MS on the basis of the reconstructed ion chromatograms (mlz 247). ...