Kinetically controlled ring-closing metathesis: synthesis of a potential scaffold for 12-membered salicylic macrolides.
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.
Matsuya
Yuji
Y
Graduate School of Medicine and Pharmaceutical Sciemces, University of Toyama, Toyama, Japan. matsuya@pha.u-toyama.ac.jp
Takayanagi
Sho-ichi
S
Nemoto
Hideo
H
D007700:Kinetics; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D012459:Salicylates / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D018942:Macrolides; D012459:Salicylates