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

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Goerdeler,  Felix
Oren Moscovitz, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Moscovitz,  Oren       
Oren Moscovitz, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Budde, S., Goerdeler, F., Floß, J., Kreitmeier, P., Hicks, E. F., Moscovitz, O., et al. (2020). Visible-light mediated oxidative ring expansion of anellated cyclopropanes to fused endoperoxides with antimalarial activity. Organic Chemistry Frontiers, 7(14), 1789-1795. doi:10.1039/D0QO00168F.


Cite as: https://hdl.handle.net/21.11116/0000-0006-3E73-4
Abstract
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.