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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
First total synthesis of 7-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one (a diarylheptanoid)
Gangapuram Balraju1, Prakash Gupta Tanguturi1, Kashamalla Chinna Ashalu1
1Department of Chemistry, School of Science, Indrashil University, Mehsana, Gujarat, India.
Abstract:
Herein, we demonstrate the first total synthesis of a natural product, 7-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one using the commercially available starting materials 1,2- dimethoxy benzene and vanillin with 20% overall yield in 15 steps. The present synthesis employs classical reactions such as Friedel-Crafts acylation, Clemmensen reduction, halogenation, reduction of carboxylic acid, functional group interconversion and tosmic reagent followed by hydrolysis are the key steps. The natural product, 7-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one was isolated from the husks of Green walnut (Juglans mandshurica maxim.).
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