Stephan Beduerftig, Manuela Weigl, B. Wünsch
Jun 11, 2001
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Influential Citations
9
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract A novel three-step synthesis of 4-substituted-(1-benzylpiperazin-2-yl)methanols 5a – 5c is described starting from the methyl ester of the proteinogenic amino acid ( S )-serine, which involves the diastereomeric oxazolidine derivatives 11a – 11c as key intermediates. 5b and 5c were transformed into the chiral, non-racemic bicyclic lactams 14b and 14c via Swern oxidation followed by Wittig reaction and subsequent hydrogenation. In the screening for central nervous system receptor affinity the butyl derivative 14b was found to have promising interaction with σ 1 -receptors ( K i =345 nM).