An Efficient Large-Scale Synthesis of EDP-420, a First-in-Class Bridged Bicyclic Macrolide (BBM) Antibiotic Drug Candidate

Autor:	Yat Sun Or, Zhigang Chen, Datong Tang, Heejin Kim, Yonghua Gai, Zhe Wang, Guoqiang Wang, Guoyou Xu, Ly Tam Phan
Rok vydání:	2010
Předmět:	Antibiotic drug Olefin fiber Bicyclic molecule Drug candidate Stereochemistry Organic Chemistry Cleavage (embryo) Oxime Combinatorial chemistry chemistry.chemical_compound chemistry Acetylation Physical and Theoretical Chemistry Oxidative cleavage
Zdroj:	Organic Process Research & Development. 14:504-510
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op900228u
Popis:	A multistep, practical, and cost-effective synthesis of novel bridged bicyclic macrolide drug candidate EDP-420 (1) is described. Starting from inexpensive and commercially available erythromycin A 9-oxime, the current chemical process involves a series of transformations: triacetylation, Pd-catalyzed O,O-bis-allylation (bridge formation), acid-catalyzed sugar cleavage, oxime reduction, acetylation, Os-catalyzed bridge olefin oxidative cleavage, Corey−Kim oxidation, bridge oxime formation, deprotection, and final purification. Multikilogram quantities have been synthesized.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bef25fede5f95fbfd1ff01d49f540090 https://doi.org/10.1021/op900228u Zobrazit plný text záznamu