title: Synthesis of eukaryotic translation elongation inhibitor lactimidomycin via Zn(II)-mediated Horner-Wadsworth-Emmons macrocyclization.
abstract: An enantioselective synthesis of potent eukaryotic translation elongation inhibitor lactimidomycin has been accomplished in 21 linear steps. This synthesis features a Zn(II)-mediated Horner-Wadsworth-Emmons reaction that could be executed on a large scale to provide the highly strained 12-membered lactimidomycin macrolactone.
authors.affiliation: Department of Chemistry, University of Michigan , Ann Arbor, Michigan 48109, United States.
authors.forename: Brian J
authors.initials: BJ
authors.lastname: Larsen
authors.forename: Zhankui
authors.initials: Z
authors.lastname: Sun
authors.forename: Pavel
authors.initials: P
authors.lastname: Nagorny
mesh_terms: D039642:Eukaryotic Initiation Factors / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D039642:Eukaryotic Initiation Factors; D007783:Lactones; D018942:Macrolides; D010881:Piperidones; C077633:lactimidomycin; D015032:Zinc