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