Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-Glucose-Derived aziridine-2-carboxylate approach
| Title | Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-Glucose-Derived aziridine-2-carboxylate approach |
| Publication Type | Journal Article |
| Year of Publication | 2007 |
| Authors | Kumar, KSAjish, Chaudhari, VD, Puranik, VG, Dhavale, DD |
| Journal | European Journal of Organic Chemistry |
| Issue | 29 |
| Pagination | 4895-4901 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 1434-193X |
| Keywords | asymmetric dihydroxylation (AD), Iminosugars, indolizidine, N-methylmorpholine, N-oxide (NNIO) |
| Abstract | D-Glucose -derived aziridine-2-carboxylate I was converted into a-amino aldehyde 7, which, after Wittig olefination, asymmetric dihydroxylation, hydrogenation followed by LiAlH4 reduction, and N-Cbz protection, afforded two diastereomeric pyrrolidines 11a and 11b with sugar appendages. Removal of the 1,2-acetonide functionality in 11a/11b and reductive animation gave the pentahydroxyindolizidine alkaloids 6g and 6h, respectively, with (S) absolute configurations at the ring junctions. The glycosidase inhibitory activities of these compounds were studied. |
| DOI | 10.1002/ejoc.200700461 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.068 |
Divison category:
Center for Material Characterization (CMC)
Physical and Materials Chemistry