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Synthesis of specifically deuteriated 9- and 13-demethylretinals

✍ Scribed by Ellen M. M. van den Berg; Arie van der Bent; Johan Lugtenburg

Book ID
104589156
Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
933 KB
Volume
109
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

(13–^2^H) 13‐Demethylretinal, (11,12,13‐^2^H,) 13‐demethylretinal, (9‐^2^H)9‐demethylretinal and (9,10‐^2^H~2~)9‐demethylretinal were prepared in all‐E, 9__Z__, 11__Z__ and 13__Z__ isomeric form with high deuterium incorporation. In the synthesis of (9,10‐^2^H~2~)9‐demethylretinal, a Horner‐Emmons reaction with deuteriated diethyl (cyanomethyl)phosphonate was used. This synthon was subsequently used for the synthesis of (10‐^2^H)‐ and (14‐^2^H)retinal in high yield and with high deuterium incorporation. From the ^13^C NMR spectra of the demethylretinals (all‐E, 9__Z__ and 13__Z__), he effect of a methyl group on the ^13^CNMR parameters of polyene‐chain carbons was determined.

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