title: Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis.
abstract: New pleuromutilin-like compounds were synthesized in approximately 11 steps from 3-allylcyclopent-2-enone by a strategy featuring sequential carbonyl addition reactions. Several analogs possessing the C14 tiamulin ester side chain displayed activity in a Mycobacterium tuberculosis mc(2)7000 assay. The results described herein provide a basis for further efforts to expand the structural and stereochemical diversity of the pleuromutilin class of bacterial protein synthesis inhibitors through advances in chemical synthesis.
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, New Jersey 08544, USA.
authors.forename: Stephen D
authors.initials: SD
authors.lastname: Lotesta
authors.forename: Junjia
authors.initials: J
authors.lastname: Liu
authors.forename: Emma V
authors.initials: EV
authors.lastname: Yates
authors.forename: Inna
authors.initials: I
authors.lastname: Krieger
authors.forename: James C
authors.initials: JC
authors.lastname: Sacchettini
authors.forename: Joel S
authors.initials: JS
authors.lastname: Freundlich
authors.forename: Erik J
authors.initials: EJ
authors.lastname: Sorensen