One-Step Synthesis of Furan Rings from α‑Isopropylidene Ketones Mediated by Iodine/DMSO: An Approach to Potent Bioactive Terpenes

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...

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Veröffentlicht in:Journal of organic chemistry 2019-06, Vol.84 (11), p.6886-6894
Hauptverfasser: Salihila, Jonida, Silva, Lúcia, Pérez del Pulgar, Helena, Quílez Molina, Ana, González-Coloma, Azucena, Olmeda, A. Sonia, Quílez del Moral, José F, Barrero, Alejandro F
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00704