Semisynthesis of an Antifungal Lipopeptide Echinocandin

Autor:	Michel Journet, David L. Hughes, Robert D. Larsen, Thomas R. Verhoeven, Dongwei Cai, Paul J. Reider, Lisa DiMichele
Rok vydání:	1999
Předmět:	Echinocandin Stereochemistry Organic Chemistry Lipopeptide Semisynthesis chemistry.chemical_compound chemistry Amide Hemiaminal medicine Side chain Stereoselectivity Amine gas treating medicine.drug
Zdroj:	The Journal of Organic Chemistry. 64:2411-2417
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo9822232
Popis:	Compound 1 is a macrocyclic lipopeptide belonging to the echinocandin family, which has been effective in treating systemic fungal infections. In this paper, we report a unique regio-, chemo-, and stereoselective synthesis of 1 in four steps from the deacylated nucleus 3 in an impressive 83% overall yield. Highlights of this synthesis include a selective reduction of the amide to the amine and a highly stereoselective (99:1 α/β) introduction of the 2-aminoethyl hemiaminal. In addition, the synthesis of the naphthoyl side chain was accomplished in three steps in 79% overall isolated yield from commercially available 6-bromo-2-naphthol.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c24feef2d818ccc67c158a706098fbaf https://doi.org/10.1021/jo9822232 Zobrazit plný text záznamu