One-Step Synthesis of Furan Rings from α-Isopropylidene Ketones Mediated by Iodine/DMSO: An Approach to Potent Bioactive Terpenes.
Jonida SalihilaLúcia SilvaHelena Pérez Del PulgarAna Quílez MolinaAzucena González-ColomaA Sonia OlmedaJosé Francisco Quílez Del MoralAlejandro F BarreroPublished in: The Journal of organic chemistry (2019)
The system I2/dimethyl sulfoxide mediates the one-step transformation of α-isopropylidene ketones into furan rings following a biomimetic approach. This methodology has been used for the synthesis of terpene furans such as mintfurane, curzerene, atractylon, and isoatractylon, all of them possessing interesting biological activities. The synthesis of linderazulene directly from 4,5-epoxygermacrone via a cascade reaction shows the potential of this protocol. Additionally, this compound proved to show significant ixodicidal activity.