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Preparation of all trans ‐retinoic‐11‐ 3 H acid and all trans ‐retinyl‐11‐ 3 H acetate

1981; Wiley; Volume: 18; Issue: 8 Linguagem: Inglês

10.1002/jlcr.2580180803

1099-1344

H. H. Kaegi, Joseph I. DeGraw,

Carbohydrate Chemistry and Synthesis

Abstract Trans ‐ionylidineacetaldehyde‐1‐ 3 H ( 3 ) was obtained by reduction of unlabeled aldehyde ( 1 ) with lithium borotritide, followed by reoxidation of the tritio alcohol ( 2 ). Condensation of aldehyde ( 3 ) with triethyl 3‐methyl‐4‐phosphonocrotonate ( 7 ), followed by saponification of the retinoic ethyl ester ( 8 ), afforded trans ‐retinoic‐11‐ 3 H acid ( 9 ). Esterification of the crystalline acid with diazomethane, and subsequent reduction of the methyl trans ‐retinoate‐11‐ 3 H with lithium aluminum hydride, yielded trans ‐retinol‐11‐ 3 H, which was acetylated in situ to give trans ‐retinyl‐11‐ 3 H acetate ( 10 ).