Semisynthesis of 8-prenylquercetin, and 8-prenyl-3,7,3’,4’-tetramethoxyflavanol & 3,5,7,3’,4’-pentahydroxy-6-(2-methylbut-3-en-2-yl )flavanol from rutin

Authors

  • Van-Son Nguyen, Vo Thanh Cong, T. T. Nha Tran

Abstract

-The novel semisynthesis of 8-prenylquercetin (1),
3,5,7,3’,4’-pentahydroxy-6-(2-methylbut-3-en-2-yl)flavanol (2) and
8-prenyl-3,7,3’,4’-tetramethoxyflavanol (3) were three naturally occurring prenylat. They have been
known such as having an important activity fighting certain human cancer cell lines. The synthesis
process was performed through hydrolysis of glycosidic bond from the corresponding flavanone
glycoside rutin, methoxymethyl protection or regioselective methylation, O-prenylation,
microwave-assistance Claisen rearrangement, and the type of protective group with overall yields
25%, 8% and 23%, respectively. In which the important method of synthesis process was the support of
the microwave system, to which the Claisen rearrangement formed 8-prenylated flavanols or
6-(2-methylbut-3-en-2-yl)flavanol from 5-O-prenylflavanols. The structural compositions of these
compounds were reported in the study by modern physicochemical analysis (1H-NMR, 13C-NMR, and
MS).

Published

2020-11-01

Issue

Section

Articles