Development of a Kilogram-Scale Asymmetric Synthesis of a Potent DP Receptor Antagonist

Autor:	Peter E. Maligres, Bob Reamer, Cecile G. Savarin, Guy R. Humphrey, Matthew T. Tudge, Katherine DiFelice, David M. Tellers, D. L. Hughes
Rok vydání:	2010
Předmět:	Indole test chemistry.chemical_classification Ketone Stereochemistry Organic Chemistry Asymmetric hydrogenation Antagonist Enantioselective synthesis Catalysis chemistry.chemical_compound Thioether chemistry Intramolecular force Physical and Theoretical Chemistry
Zdroj:	Organic Process Research & Development. 14:787-798
ISSN:	1520-586X 1083-6160
Popis:	An efficient asymmetric synthesis of a unique sulfenylated prostaglandin DP receptor antagonist candidate is described. The synthesis is characterized by a novel intramolecular Friedel−Crafts cyclization of an imino-pyrrole to prepare the azaindole core. Other key steps include a highly selective Horner−Wadsworth−Emmons olefination of a tricyclic ketone intermediate and subsequent catalytic asymmetric hydrogenation of a trisubstituted α,β-unsaturated ester to install the chirogenic center. Finally, a new indole sulfenylation protocol was developed to install the aromatic thioether functionality in good yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4bb3ebeb641a62cc3849869a7d9945b4 https://doi.org/10.1021/op100008m Zobrazit plný text záznamu