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

Research output: Contribution to journalArticle

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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 languageEnglish
Pages (from-to)201-206
Number of pages6
JournalTetrahedron
Volume31
Issue number3
DOIs
StatePublished - Jan 1 1975
Externally publishedYes

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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

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 journalArticle

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