Synthesis of 9Z-9-substituted retinoic acids by palladium catalyzed coupling reaction of a vinyl triflate with alkenyl stannanes.
Palladium catalyzed cross coupling reactions of a vinyl triflate intermediate and various alkenyl stannanes afforded trisubstituted Z-olefins stereoselectively in high yields. These olefins were then converted to the corresponding 9Z-retinoic acids via Horner-Emmons reaction and subsequent basic hydrolysis in excellent yields.
Wada
A
A
Kobe Pharmaceutical University, Higashinada, Japan. a-wada@kobepharma-u.ac.jp
Nomoto
Y
Y
Tano
K
K
Yamashita
E
E
Ito
M
M
D002384:Catalysis; D007202:Indicators and Reagents; D008698:Mesylates / Q000737:chemistry*; D010165:Palladium; D013056:Spectrophotometry, Ultraviolet; D017971:Tin Compounds; D014212:Tretinoin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D014753:Vinyl Compounds / Q000737:chemistry*
D007202:Indicators and Reagents; D008698:Mesylates; D017971:Tin Compounds; D014753:Vinyl Compounds; C031525:stannane; D014212:Tretinoin; D010165:Palladium