Expeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase
| Title | Expeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Chanda, BM, Sulake, RS |
| Journal | Tetrahedron Letters |
| Volume | 46 |
| Issue | 38 |
| Pagination | 6461-6463 |
| Date Published | SEP |
| Type of Article | Article |
| ISSN | 0040-4039 |
| Keywords | 4-hydroxybenzaldehyde, marine alkaloid, mycothiol-S-conjugate amidase |
| Abstract | A quick, economic synthesis of the alkaloid 1, an inhibitor of mycothiol-S-conjugate amidase (MCA) is reported. Starting from low-cost, commercially available 4-hydroxybenzaldehyde, the nine-step synthesis involved dibromination and coupling with N-acetylglycine to give a stable methyloxazole intermediate 5 which was hydrolyzed, oximated and coupled to agmatine to yield the oxime in -30% overall yield. It was not necessary to protect the oxime in the synthetic sequence thereby circumventing a deprotection step. (c) 2005 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2005.07.109 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.347 |
Divison category:
Organic Chemistry
