Prenilasi Senyawa β-Diketon sebagai Prekursor 3-Prenilflavon

Abstract

One group of flavonoids that has not been commonly synthesized is 3- prenylflavone. The main objective of this experiment was to synthesize precursor of 3-prenylflavone. Firstly, β-diketone was synthesized via 4 steps from phenol as starting compound with total yield of 24%. Prenylation of β-diketone with prenyl bromide and K2CO3 base produced 4 fractions which were separated by using preparative thin layer chromatography (PTLC) with n-hexane:EtOAc (8:2) as the eluent. Fraction with Rf = 0.80 was further separated by using preparative PTLC with n-hexane:EtOAc (99:1) as the eluent. Two fractions were obtained with Rf = 0.38 and 0.42. The first fraction has been characterized as diprenylated β-diketone with 49% yield. Application of protecting group on the phenolic OH group in β- diketone are needed to obtain monoprenylated β-diketone which can be further cyclized into 3-prenylflavone