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

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 the 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 includ 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

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Publication details

The article was received on 25 Jul 2019, accepted on 14 Aug 2019 and first published on 14 Aug 2019


Article type: Paper
DOI: 10.1039/C9OB01645G
Org. Biomol. Chem., 2019, Accepted Manuscript

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    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, Accepted Manuscript , DOI: 10.1039/C9OB01645G

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