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Preparation of all‐ trans ‐retinal‐11‐ 3 H and all‐ trans ‐retinyl‐11‐ 3 H acetate
Author(s) -
Kaegi Hans H.,
Bupp James E.,
Degraw Joseph I.
Publication year - 1982
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580190606
Subject(s) - chemistry , aldehyde , retinal , lithium (medication) , yield (engineering) , alcohol , acetylation , ethanol , medicinal chemistry , organic chemistry , biochemistry , medicine , materials science , metallurgy , catalysis , gene
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.