First total synthesis of 7-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one (a diarylheptanoid)

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 (<i>Juglans mandshurica maxim.</i>).