TY - JOUR
T1 - 7-Cis isomers of retinal via 7-cis- and 7,9-dicis-β-C18-tetraene ketones. New geometric isomers of vitamin A and carotenoids-I
AU - Ramamurthy, V.
AU - Liu, R. S.H.
PY - 1975
Y1 - 1975
N2 - Based catalyzed condensation of 7-cis- or 7,9-dicis-β-ionylideneacetaldehyde with acetone gave either 7-cis or 7,9-dicis-β-C18-tetraene ketone. Reaction of the tetraene ketone mixture with diethyl cyanomethylphosphonate gave a mixture of 4 isomers of retinonitrile, all believed to have the 7-cis geometry. Partial redution of the retinonitrile mixture with di-isobutylaluminum hydride gave a mixture of retinal isomers. Repeated column chromatography resulted in partial separation of the retinal isomers. Based on NMR data the geometry of the isomers prepared are believed to be 7-cis, 7,13-dicis, and 7,9,13-tricis.
AB - Based catalyzed condensation of 7-cis- or 7,9-dicis-β-ionylideneacetaldehyde with acetone gave either 7-cis or 7,9-dicis-β-C18-tetraene ketone. Reaction of the tetraene ketone mixture with diethyl cyanomethylphosphonate gave a mixture of 4 isomers of retinonitrile, all believed to have the 7-cis geometry. Partial redution of the retinonitrile mixture with di-isobutylaluminum hydride gave a mixture of retinal isomers. Repeated column chromatography resulted in partial separation of the retinal isomers. Based on NMR data the geometry of the isomers prepared are believed to be 7-cis, 7,13-dicis, and 7,9,13-tricis.
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U2 - 10.1016/0040-4020(75)85066-6
DO - 10.1016/0040-4020(75)85066-6
M3 - Article
AN - SCOPUS:0016433587
VL - 31
SP - 201
EP - 206
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 3
ER -