title: Concise total synthesis of the potent translation and cell migration inhibitor lactimidomycin.
abstract: An efficient total synthesis of the antiproliferative macrolide and cell migration inhibitor lactimidomycin (3) is reported, which relies on the performance of ring closing alkyne metathesis (RCAM). The strained 12-membered 1,3-enyne 21 as the key intermediate was forged with the aid of [(Ph(3)SiO)(3)Mo≡CPh]·OEt(2) (27) as the most effective member of a new generation of powerful alkyne metathesis catalysts. 21 was elaborated to the target by a ruthenium catalyzed trans-hydrosilylation/proto-desilylation sequence and a highly diastereoselective Mukaiyama aldol reaction controlled by oxazaborolidinone 29 as strategic operations.
authors.affiliation: Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany.
authors.forename: Kevin
authors.initials: K
authors.lastname: Micoine
authors.forename: Alois
authors.initials: A
authors.lastname: Fürstner
mesh_terms: D000818:Animals; D002465:Cell Movement / Q000187:drug effects*; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000494:pharmacology; D010881:Piperidones / Q000138:chemical synthesis* / Q000494:pharmacology; D014176:Protein Biosynthesis / Q000187:drug effects*
chemical_list: D018942:Macrolides; D010881:Piperidones; C077633:lactimidomycin