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Issue 35, 2019
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Z-isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis

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Abstract

Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to correlate the experimentally observed Z-isomer distribution of retinoids with the energies of chemically important intermediates, which include ground- and excited-state potential energy surfaces. We also demonstrate the application of the current method by synthesizing gram-scale quantities of 9-cis-retinyl acetate 9Z-a. Operational simplicity and gram-scale ability make this chemistry a very practical solution to the problem of Z-isomer retinoid synthesis.

Graphical abstract: Z-isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis

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Supplementary files

Article information


Submitted
25 Jul 2019
Accepted
14 Aug 2019
First published
14 Aug 2019

Org. Biomol. Chem., 2019,17, 8125-8139
Article type
Paper

Z-isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis

S. Kahremany, C. L. Sander, G. P. Tochtrop, A. Kubas and K. Palczewski, Org. Biomol. Chem., 2019, 17, 8125
DOI: 10.1039/C9OB01645G

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