Expeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase

TitleExpeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase
Publication TypeJournal Article
Year of Publication2005
AuthorsChanda, BM, Sulake, RS
JournalTetrahedron Letters
Volume46
Issue38
Pagination6461-6463
Date PublishedSEP
Type of ArticleArticle
ISSN0040-4039
Keywords4-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.

DOI10.1016/j.tetlet.2005.07.109
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.347
Divison category: 
Organic Chemistry