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Synthesis of 9-CD3-9-cis-retinal cofactor of isorhodopsin

Author:
Navidi, Mozhgan, Yadav, Shreya, Struts, Andrey V., Brown, Michael F., Nesnas, Nasri
Source:
Tetrahedron letters 2018 v.59 no.51 pp. 4521-4524
ISSN:
0040-4039
Subject:
alcohols, beta-ionone, chemical structure, deuterium, oxidation, vitamin A
Abstract:
We report the synthesis of 9-CD3-9-cis-retinal via a six-step procedure from β-ionone. The steps involve an initial deuteration of the methyl ketone of β-ionone followed by two consecutive Horner-Wadsworth-Emmons (HWE) coupling reactions and their corresponding DIBAL reductions. A final oxidation of the allylic alcohol of the retinol leads to the target compound. This deuterium labeled retinoid is an important cofactor for studying protein-retinoid interactions in isorhodopsin.
Agid:
6232178