title: Kinetically controlled ring-closing metathesis: synthesis of a potential scaffold for 12-membered salicylic macrolides.
abstract: For the synthesis of a 12-membered salicylic macrolide scaffold, ring-closing metathesis (RCM) of a omega-diene compound was planned. The stereochemical outcome of the RCM reaction changed depending on the type of Ru catalyst that was used; a "first-generation" Grubbs catalyst produced exclusively the E isomer and "second-generation" catalysts provided a mixture of the E and Z isomers under kinetic control (not thermodynamic control). Considerations for the E/Z selectivity are described.
authors.affiliation: Graduate School of Medicine and Pharmaceutical Sciemces, University of Toyama, Toyama, Japan. matsuya@pha.u-toyama.ac.jp
authors.forename: Yuji
authors.initials: Y
authors.lastname: Matsuya
authors.forename: Sho-ichi
authors.initials: S
authors.lastname: Takayanagi
authors.forename: Hideo
authors.initials: H
authors.lastname: Nemoto
mesh_terms: D007700:Kinetics; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D012459:Salicylates / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D018942:Macrolides; D012459:Salicylates