Visible-light mediated oxidative ring expansion of anellated cyclopropanes to fused endoperoxides with antimalarial activity

A visible light mediated ring expansion of readily available carbo- and heterocyclic anellated cyclopropanes by molecular oxygen at ambient pressure has been developed. Tolerating a variety of functional groups, the reaction yields fused 1,2-dioxolanes, which were tested for antimalarial activity gi...

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Veröffentlicht in:Organic Chemistry Frontiers 2020-07, Vol.7 (14), p.1789-1795
Hauptverfasser: Budde, Simon, Goerdeler, Felix, Floß, Johannes, Kreitmeier, Peter, Hicks, Elliot F., Moscovitz, Oren, Seeberger, Peter H., Davies, Huw M. L., Reiser, Oliver
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Sprache:eng
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Zusammenfassung:A visible light mediated ring expansion of readily available carbo- and heterocyclic anellated cyclopropanes by molecular oxygen at ambient pressure has been developed. Tolerating a variety of functional groups, the reaction yields fused 1,2-dioxolanes, which were tested for antimalarial activity given their close analogy to the active principle of approved drugs such as artemisinin.
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/D0QO00168F