Abstract

We hereby report the biomimetic synthesis of three flavonoid alkaloids, namely 8-(2″-pyrrolidinon-5″-yl)quercetin, 6-(2″-pyrrolidinon-5″-yl)-(–)-epicatechin and 8-(2″-pyrrolidinon-5″-yl)-(–)-epicatechin. These known natural products were prepared via an acid-catalysed regioselective phenolic Mannich reaction involving the electrophilic attack of an N-acyliminium ion on the corresponding flavonoidal precursors. The products were purified by preparative HPLC. The reactions showed high C8-regioselectivity. The major isomers of the synthesized flavonoid alkaloids were further characterized in terms of their medicinal-chemical properties.

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