Issue 14, 2020

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
05 Feb 2020
Accepted
06 Apr 2020
First published
09 Apr 2020

Org. Chem. Front., 2020,7, 1789-1795

Author version available

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

S. Budde, F. Goerdeler, J. Floß, P. Kreitmeier, E. F. Hicks, O. Moscovitz, P. H. Seeberger, H. M. L. Davies and O. Reiser, Org. Chem. Front., 2020, 7, 1789 DOI: 10.1039/D0QO00168F

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