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Preparation of all-trans-retinal-11-3H and all-trans-retinyl-11-3H acetate

✍ Scribed by Hans H. Kaegi; James E. Bupp; Joseph I. Degraw

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
314 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

trans‐Ionylideneacetaldehyde‐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 diethyl 3‐cyano‐2‐methylprop‐2‐enylphosphonate (7) afforded retinonitrile‐11‐^3^H (8) which was smoothly reduced to trans‐retinal‐11‐^3^H (9) with diisobutylaluminum hydride. Reduction of retinal (9) with lithium borohyride followed by acetylation gave retinyl‐11‐^3^H‐acetate in excellent yield.

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