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

✍ Scribed by Hans H. Kaegi; Joseph I. Degraw

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
300 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

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).

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