First total synthesis of artepillin C established by o,o'-diprenylation of p-halophenols in water.
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.
Uto
Yoshihiro
Y
Department of Biological Science & Technology, Faculty of Engineering, The University of Tokushima, Minamijosanjima-cho 2-1, Tokushima, 770-8506 Japan hori@bio.tokushima-u.ac.jp
Hirata
Akihiko
A
Fujita
Tomoya
T
Takubo
Syunsuke
S
Nagasawa
Hideko
H
Hori
Hitoshi
H
D001938:Brazil; D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry*; D010666:Phenylpropionates / Q000138:chemical synthesis* / Q000737:chemistry; D011429:Propolis / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D002934:Cinnamates; D010636:Phenols; D010666:Phenylpropionates; D014867:Water; C102259:artepillin C; D011429:Propolis