Navidi Mozhgan, Yadav Shreya, Struts Andrey V, Brown Michael F, Nesnas Nasri
Department of Biomedical & Chemical Engineering & Sciences, Florida Institute of Technology, Melbourne, Florida 32901, USA.
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Tetrahedron Lett. 2018 Dec 19;59(51):4521-4524. doi: 10.1016/j.tetlet.2018.11.034. Epub 2018 Nov 10.
We report the synthesis of 9-CD-9--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.
我们报道了通过从β-紫罗兰酮出发的六步合成法制备9-反式-视黄醛。这些步骤包括β-紫罗兰酮甲基酮的初始氘代，随后是连续的两次霍纳-沃兹沃思-埃蒙斯（HWE）偶联反应及其相应的二异丁基氢化铝还原反应。视黄醇烯丙醇的最终氧化反应生成目标化合物。这种氘标记的类视黄醇是研究异视紫红质中蛋白质-类视黄醇相互作用的重要辅助因子。
