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

Christophe Daeppen | Zendy; Marcel Kaiser | Zendy; Markus Neuburger | Zendy; Karl Gademann | Zendy

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

Author(s) -

Christophe Daeppen,

Marcel Kaiser,

Markus Neuburger,

Karl Gademann

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b02773

Subject(s) - chemistry , cycloaddition , olefin fiber , yield (engineering) , alkylation , combinatorial chemistry , hemiacetal , stereochemistry , organic chemistry , catalysis , materials science , metallurgy

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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