Highly convergent, stereospecific synthesis of 11-cis-retinoids by metal-catalyzed cross-coupling reactions of (Z)-1-alkenylmetals.
A stereospecific synthesis of 11-cis-retinoids has as its key step the hitherto unexplored palladium-catalyzed cross-coupling of trans-trienyl electrophiles and (1Z,3E)-penta-1,3-dienyl boronates (a Suzuki-Miyaura reaction) or stannanes (a Stille reaction). This highly convergent approach constitutes the first application of cis-organometallic moieties to the synthesis of 11-cis-retinoids and represents a general, straightforward route to the visual chromophore.
López
Susana
S
Departamento de Química OrgAnica, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain. qosuslop@usc.es
Montenegro
Javier
J
Saá
Carlos
C
D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012176:Retinoids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry
D001897:Boronic Acids; D009942:Organometallic Compounds; D012176:Retinoids; D017971:Tin Compounds; C031525:stannane; D010165:Palladium