Synthesis of (5S)-TricyclicPenems as Novel and Potent Inhibitors of Bacterial Signal Peptidases

Autor:	Leo Grinius, Nick K. Kim, Glen E. Mieling, Charles M. Morris, Thomas P. Demuth, X. Eric Hu, Cynthia D. Wallace
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Reaction conditions Signal peptidase chemistry Stereochemistry Organic Chemistry Intramolecular cyclization Molecule Lewis acids and bases Catalysis Tricyclic Ring strain
Zdroj:	Synthesis. 2003:1732-1738
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2003-40882
Popis:	(5S)-Tricyclic penems were synthesized for the first time via intramolecular cyclization of penem epoxy amides catalyzed by a weak Lewis acid [Mg(ClO 4 ) 2 ]. Due to the high degree of ring strain in these molecules, mild reaction conditions were developed to successfully construct penem intermediates and the tricyclic penem final products. These tricyclic penems and other newly synthesized (5S)-penem esters and amides exhibited good-to-high potency when tested as inhibitors of bacterial signal peptidases.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::cefb686654910e27f26541476cd5456e https://doi.org/10.1055/s-2003-40882 Zobrazit plný text záznamu