Fine tuning of a reported synthetic route for biologically active flavonoid, baicalein.
A modified procedure of a previous synthetic route for baicalein was developed in order to obtain more than ten grams of baicalein for in vivo test. There were several difficulties in applying the published experimental procedures for a large scale of synthesis. The modified synthetic work was successfully accomplished by reducing amount of strong Lewis acid in Fries rearrangement and using tetrabutylammonium iodide as an additive to speed up the demethylation reaction in refluxing HBr into completion.
Kim
Sanghee
S
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 110-460, Korea.
Sohn
Dae Won
DW
Kim
Youn Chul
YC
Kim
Soon-Ai
SA
Lee
Sang Kook
SK
Kim
Hak Sung
HS
D002626:Chemistry, Pharmaceutical / Q000379:methods; D002855:Chromatography, Thin Layer; D003640:Dealkylation; D004365:Drugs, Chinese Herbal / Q000138:chemical synthesis*; D044950:Flavanones / Q000138:chemical synthesis*; D018054:Hydrobromic Acid / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D015203:Reproducibility of Results; D013678:Technology, Pharmaceutical / Q000379:methods*; D013696:Temperature; D013997:Time Factors
D004365:Drugs, Chinese Herbal; D044950:Flavanones; D000644:Quaternary Ammonium Compounds; D018054:Hydrobromic Acid; C006680:baicalein; C009405:tetrabutylammonium