Synthesis of substituted 3-hydroxy-4-alkoxycarbonyl-2-azetidinones

✍ Scribed by Teodozyj Kolasa; Marvin J. Miller

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 189 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95994-x

✦ Synopsis

A short chemical process is described for the synthesis of optically active 3y roxy-4-alkoxycarbonyl-Z-azetidinones (R-lactams) from L-tartaric acid. Tartaric acid is an extremely useful and versatile member of the chiral pool. Since nearly any type of f+hydroxy acid can be converted to a 8-lactam (2-azetidinone) by the hydroxamate method,l tartaric acid was considered an attractive precursor of important optically active derivatives of 3-hydroxy-4-alkoxycarbonyl-2-azetidinones 2. The main problem with the utilization of tartaric acid derivatives for the synthesis of 6-lactams was anticipated to be the differentiation of the two carboxylic acid and two hydroxyl groups. A recent report on the the synthesis of 6-lactams from tartaric acid required enzymatic methods for this differentiation. 2 Herein we describe a totally chemical approach to the complete differentiation of all of the functional groups of L-(2R,3R)-(+)-tartaric acid and the application to the synthesis of optically active substituted 3-hydroxy-4-alkoxycarbonyl-E-azetidinones.