Total synthesis of prenylated and non-prenylated flavonoid from natural products: Synthesis of lupinifolin and 5, 7-dihydroxy-2-(2-hydroxy-4-methoxyphenyl) benzopyran-4-one

Abstract

Based on World Health Organization reports, resistance of bacteria to renowned antibiotics is a major global health challenge today and in the future. Synthetic compounds tend to display better biological activity in comparison with the parent natural product. The authors report here short communication of a series of Prenyl substituted compounds was synthesized. Synthetic lupinifolin and 5,7-dihydroxy-2-(2-hydroxy-4-methoxyphenyl) benzopyran-4-one were prepared and characterized using ¹H and ¹³C NMR spectroscopy, Infrared spectroscope and melting point. And detailed mechanism of Lupinifolin is discussed. 2, 4, 6-trihydroxy-3-prenylacetophenone, 2-hydroxy-4, 6-dimethoxy-3-prenylacetophenone and chaclone indtermediates were synthesized. The synthetic compounds obtained as a yellow powder and brownish powder were confirmed to be Lupinifolin and 2,3-Dihydro-5,7-dihydroxy-2-(2,4-dihydroxyphenyl)-H-1-benzopyran-4-one respectively by comparing the obtained IR and ¹H-NMR spectral data with the literature. Hence the author’s developed ecofriendly route for the synthesis of Prenylated flavonoid’s.

Keywords: Natural product, Synthetic compounds, Biological activity, and prenylated flavonoids.