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Conversion of glucuronic acid glycosides to novel bicyclic beta-lactams
Timothy B Durham1, Marvin J Miller
1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.
Abstract:
[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.
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