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Preparation of antimalarial endoperoxides by a formal [2 + 2 + 2] cycloaddition

Daeppen, Christophe and Kaiser, Marcel and Neuburger, Markus and Gademann, Karl. (2015) Preparation of antimalarial endoperoxides by a formal [2 + 2 + 2] cycloaddition. Organic letters, 17 (21). pp. 5420-5423.

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Official URL: http://edoc.unibas.ch/41279/

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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.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel
Item Type:Article, refereed
Publisher:American Chemical Society
ISSN:1523-7060
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:30 Jun 2016 11:02
Deposited On:11 Apr 2016 12:58

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