Preparation of 11,14-epoxy-bridged and isomeric chain-demethylated retinals. 13-Demethyl-11,14-epoxy-, 9-demethyl-, 13-demethyl- and 9,13-bisdemethyl-retinals

Autor:	M. Muradin-Szweykowska, J. M. L. Courtin, Johan Lugtenburg, A. D. Broek
Rok vydání:	1983
Předmět:	Acetate synthesis General Chemistry Epoxy Furfural High-performance liquid chromatography Solvent chemistry.chemical_compound chemistry Bromide visual_art Wittig reaction visual_art.visual_art_medium Organic chemistry Saponification
Zdroj:	Recueil des Travaux Chimiques des Pays-Bas. 102:46-51
ISSN:	0165-0513
DOI:	10.1002/recl.19831020107
Popis:	9-Cis- and all-trans-13-demethyl-11,14-epoxyretinyl acetate were prepared via a Wittig coupling between β-ionylidenetriphenylphosphonium bromide (1) and 5-(acetoxymethyl)furfural. Saponification of these acetates, subsequent oxidation and HPLC separation afforded pure 9-cis-and all-trans-13-demethyl-11,14-epoxyretinal. 11-Cis- and all-trans-9-demethyl-, 13-demethyl- and 9,13-bisdemethyl-retinal were prepared via the same scheme, based on the Pommer vitamin A acetate synthesis. Their photochemistry shows the same type of solvent dependence as retinal. HPLC separation of the photostationary mixtures of these retinals yielded the all-trans, 13-, 11-, 9- and 7-cis isomers in 98% purity.
Databáze:	OpenAIRE
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