Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (beta-lactam), involving a cascade sequence of reactions as a key step
| Title | Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (beta-lactam), involving a cascade sequence of reactions as a key step |
| Publication Type | Journal Article |
| Year of Publication | 2014 |
| Authors | Tiwari, DKumar, Bharadwaj, KChandra, Puranik, VG, Tiwari, DKumar |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 12 |
| Issue | 37 |
| Pagination | 7389-7396 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 1477-0520 |
| Abstract | A divergent, short, and novel total synthesis of 1,6,8a-tri-epi-castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed via a common precursor, 15, obtained from D-mannitol derived beta-lactam. The key step involves a one pot cascade sequence of trimethyl sulfoxonium ylide based cyclization of epoxy sulfonamide 14 via epoxide ring opening, one carbon homologation followed by intramolecular cyclization. |
| DOI | 10.1039/c4ob00948g |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.559 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry