Synthesis of pure methyl [(2S,3R,alpha R)-1-(3-bromo-4-methoxyphenyl)-3-(alpha-acetoxy)ethyl-4-oxoazetidin-2-carboxylate] and its enantiomer

Authors
Santa, Z Parkanyi, L Nemeth, I Nagy, J Nyitrai, J
Citation
Z. Santa et al., Synthesis of pure methyl [(2S,3R,alpha R)-1-(3-bromo-4-methoxyphenyl)-3-(alpha-acetoxy)ethyl-4-oxoazetidin-2-carboxylate] and its enantiomer, TETRAHEDR-A, 12(1), 2001, pp. 89-94
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
1
Year of publication
2001
Pages
89 - 94
Database
ISI
SICI code
0957-4166(20010205)12:1<89:SOPM[R>2.0.ZU;2-5
Abstract
Synthesis of key intermediates leading to 2-iso-oxacephems was carried out starting from L- and D-threonine. As predicted in our previous paper (Tetra hedron Lett. 1995, 36, 8303-8306) all diastereomers of 2-iso-oxacephems can be prepared from the appropriate enantiomers of the amino acid threonine. The absolute configuration of the 2,3- and alpha -carbon atoms in the beta -lactam structure was determined by X-ray crystallographic studies. (C) 200 1 Elsevier Science Ltd. All rights reserved.