PMID: 11925254Apr 2, 2002Paper

First total synthesis of artepillin C established by o,o'-diprenylation of p-halophenols in water

The Journal of Organic Chemistry
Yoshihiro UtoHitoshi Hori

Abstract

We have demonstrated that prenylation of p-halophenols was dependent on the solvent effect and succeeded in o,o'-diprenylation of p-halophenols in water. Following the Mizoroki-Heck coupling of the diprenyl-p-iodophenol 3c with methyl acrylate and then hydrolysis, we first synthesized artepillin C [3-(4-hydroxy-3,5-di(3-methyl-2-butenyl)phenyl)-2(E)-propenoic acid] (1), which is a biologically active constituent of propolis. These reactions may be applicable to the synthesis of various useful natural products such as 2,4,6-trisubstituted phenol derivatives.

References

Nov 21, 1998·Cancer Detection and Prevention·T KimotoK Mito

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Citations

Oct 2, 2003·Bioscience, Biotechnology, and Biochemistry·Hidefumi MakabeMitsuru Hirota
Jul 13, 2012·Bioscience, Biotechnology, and Biochemistry·Ryosuke MunakataKazufumi Yazaki
Apr 3, 2012·Drug Discoveries & Therapeutics·H Maruta
May 14, 2008·European Journal of Pharmacology·Niraldo PaulinoWalter A Bretz
Jun 19, 2015·Bioscience, Biotechnology, and Biochemistry·Kazuki YashiroTakeshi Sugai
Mar 18, 2011·Natural Product Reports·Antonio SalatinoMaria Luiza F Salatino
Feb 20, 2021·Journal of Chromatographic Science·Fabio GaleottiNicola Volpi

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