Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure.
Nine bioactive allylphenol (anisole) derivatives (e.g. eugenol, safrole and asaricin) present in several plants of the genus Piper have been synthesized in medium to high yield via aryl cation intermediates. This expeditious metal-free procedure involves the irradiation of the corresponding chlorophenols or chloroanisoles in a polar solvent (MeCN or, better, TFE or aqueous acetonitrile) in the presence of allyltrimethylsilane. Estragole has also been synthesized starting from the corresponding fluoroderivative and diazonium salt, though in a lower yield.
Protti
Stefano
S
Dipartimento di Chimica Organica, Università, V. Taramelli 10, 27100 Pavia, Italy.
Fagnoni
Maurizio
M
Albini
Angelo
A
D008670:Metals / Q000737:chemistry; D010636:Phenols / Q000032:analysis*; D010777:Photochemistry; D031701:Piper / Q000737:chemistry*
D008670:Metals; D010636:Phenols