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

Vaidhyanathan Ramamurthy; R. S H Liu

doi:10.1016/0040-4020(75)85066-6

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

Vaidhyanathan Ramamurthy, R. S H Liu

Research output: Contribution to journal › Article

44 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	201-206
Number of pages	6
Journal	Tetrahedron
Volume	31
Issue number	3
DOIs	https://doi.org/10.1016/0040-4020(75)85066-6
State	Published - Jan 1 1975
Externally published	Yes

Fingerprint

Carotenoids

Ketones

Vitamin A

Isomers

Acetone

Chromatography

Column chromatography

Geometry

Hydrides

Condensation

Nuclear magnetic resonance

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Ramamurthy, V., & Liu, R. S. H. (1975). 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. Tetrahedron, 31(3), 201-206. https://doi.org/10.1016/0040-4020(75)85066-6

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. / Ramamurthy, Vaidhyanathan; Liu, R. S H.

In: Tetrahedron, Vol. 31, No. 3, 01.01.1975, p. 201-206.

Research output: Contribution to journal › Article

Ramamurthy, V & Liu, RSH 1975, '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', Tetrahedron, vol. 31, no. 3, pp. 201-206. https://doi.org/10.1016/0040-4020(75)85066-6

Ramamurthy V, Liu RSH. 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. Tetrahedron. 1975 Jan 1;31(3):201-206. https://doi.org/10.1016/0040-4020(75)85066-6

Ramamurthy, Vaidhyanathan ; Liu, R. S H. / 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. In: Tetrahedron. 1975 ; Vol. 31, No. 3. pp. 201-206.

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10.1016/0040-4020(75)85066-6