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Preparation of Antimalarial Endoperoxides by a Formal [2 + 2 + 2] Cycloaddition


Daeppen, Christophe; Kaiser, Marcel; Neuburger, Markus; Gademann, Karl (2015). Preparation of Antimalarial Endoperoxides by a Formal [2 + 2 + 2] Cycloaddition. Organic Letters, 17:5420-5423.

Abstract

A formal [2 + 2 + 2] cycloaddition reaction between a 1,3-dione, an olefin, and molecular oxygen mediated by light is reported, which delivers endoperoxides in good yield through the formation of two C–O and one C–C bond in one step. The resulting 1,2-dioxanes are stable compounds and can be further derivatized at the hemiacetal position via alkylation or acetylation. All compounds have been evaluated against Plasmodium falciparum, and the best compound displayed an IC50-value of 180 nM. A potential mechanistic rationale for the formation of these compounds is presented.

Abstract

A formal [2 + 2 + 2] cycloaddition reaction between a 1,3-dione, an olefin, and molecular oxygen mediated by light is reported, which delivers endoperoxides in good yield through the formation of two C–O and one C–C bond in one step. The resulting 1,2-dioxanes are stable compounds and can be further derivatized at the hemiacetal position via alkylation or acetylation. All compounds have been evaluated against Plasmodium falciparum, and the best compound displayed an IC50-value of 180 nM. A potential mechanistic rationale for the formation of these compounds is presented.

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2 citations in Web of Science®
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Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2015
Deposited On:15 Dec 2015 13:46
Last Modified:05 Apr 2016 19:37
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
Publisher DOI:https://doi.org/10.1021/acs.orglett.5b02773

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