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New insights into the seleniranium ion promoted cyclization of prenyl and propenylbenzene aryl ethers
Authors:Serena Fiorito  Francesco Epifano  Francesca Preziuso  Vito Alessandro Taddeo  Claudio Santi  Salvatore Genovese
Affiliation:1. Dipartimento di Farmacia, Università “G. D''Annunzio” Chieti-Pescara, Via dei Vestini 31, 66100 Chieti Scalo (CH), Italy;2. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo, 06132 Perugia, Italy
Abstract:
The chromane core is widely represented in nature being part of a wide array of secondary metabolites of plant, fungal, and bacterial origin. In this paper an improved method for the chemical synthesis of differently substituted chromanes is described. Substituted 2H-1-benzopyrans have been synthesized in good to excellent yields (52–81%) by treatment of 3,3-dimethylallyl and propenylbenzene ethers of differently substituted phenols with phenylselenyl chloride.
Keywords:Carbocyclizations  Chromanes  Natural products  Organoselenium compounds  Oxyprenylated secondary metabolites
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