Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5279680 | Tetrahedron Letters | 2005 | 4 Pages |
Abstract
The d-gluco-, l-ido-, d-galacto-, and l-altro-configured glycaro-1,5-lactams 1-4 were prepared from the known tartaric anhydride 5 via the aldehyde 6. These lactams are known (1) or potential (2-4) inhibitors of β-d-glucuronidases and α-l-iduronidases. Olefination of 6 to the (E)- and (Z)-alkenes 7 or 8, followed by reagent or substrate controlled dihydroxylation, lactonization, azidation, reduction, and deprotection led in 10 steps and in overall yields of 11-20% to the title lactams.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jagadish Pabba, Andrea Vasella,