Synthesis of naturally occurring (+)-osmundalactone and 4-epi-(+)-osmundalactone from triacetyl-O-D-glucal
| Title | Synthesis of naturally occurring (+)-osmundalactone and 4-epi-(+)-osmundalactone from triacetyl-O-D-glucal |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Kotammagari, TK, Gonnade, RG, Bhattacharya, AK |
| Journal | Tetrahedron Letters |
| Volume | 56 |
| Issue | 21 |
| Pagination | 2783-2786 |
| Date Published | MAY |
| ISSN | 0040-4039 |
| Keywords | Bioactive molecules, carbohydrates, D-glucal, Ferrier rearrangement, Pyrones |
| Abstract | An efficient total synthesis of (+)-osmundalactone 1 has been achieved starting from readily available triacetyl-O-D-glucal 6 employing Ferrier rearrangement and Jones oxidation as key steps. Also, synthesis of 4-epi-(+)-osmundalactone 2 was accomplished from the common key intermediate 9. The absolute stereochemistry of (+)-osmundalactone 1 and a precursor of 4-epi-(+)-osmundalactone 2 have been established by single crystal X-ray analysis. The overall yield of compound 1 and 2 from triacetyl-O-D-glucal 6 is 13% and 8%, respectively. (C) 2015 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2015.04.038 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.347 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry