Conversion of glucuronic acid glycosides to novel bicyclic beta-lactams.
[reaction: see text] Methodology for the conversion of glucuronic acid glycosides to novel bicyclic beta-lactams is reported. Using this strategy, we prepared two novel templates suitable for use in combinatorial chemistry strategies for the construction of a number of interesting beta-lactam motifs. Key features of this strategy include a diastereoselective Ferrier reaction of a glucuronic acid glucal, selective beta-lactam ring formation using a cyclic allylic alcohol, and a chemoselective benzylic oxidation.
Durham
Timothy B
TB
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.
Miller
Marvin J
MJ
D020650:Combinatorial Chemistry Techniques; D020723:Glucuronic Acid / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D007202:Indicators and Reagents; D047090:beta-Lactams / Q000138:chemical synthesis*
D006027:Glycosides; D007202:Indicators and Reagents; D047090:beta-Lactams; D020723:Glucuronic Acid