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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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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.[1]

References

  1. First total synthesis of artepillin C established by o,o'-diprenylation of p-halophenols in water. Uto, Y., Hirata, A., Fujita, T., Takubo, S., Nagasawa, H., Hori, H. J. Org. Chem. (2002) [Pubmed]
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