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May 13-14, 2019 | Prague, Czech Republic
Chemistry and Medicinal Chemistry
9th World Congress on
Asian Journal of Biomedical and Pharmaceutical Sciences | Volume 9 ISSN: 2249-622X
Organic peroxides: From elusive intermediates to reagents and synthetic targets
Vera A Vil, Yana A Barsegyan, Maria V Ekimova, Oleg V Bityukov, Gabriel dos Passos Gomes, Igor V Alabugin
and Alexander O Terent’ev
N D Zelinsky Institute of Organic Chemistry, Russia
F or a long time, organic chemists thought about
peroxides as an explosive high energy functionality
that should be either avoided or used in selected niche
applications as radical initiators, explosives, or oxidizing
reagents. However, a recent revolution, illustrated by the
2015 Nobel Prize in Medicine, brought organic peroxide
in the spotlight as a new promising class of medicinal and
agricultural agents. In recent decades, interest to organic
peroxides has been boosted by the discovery of their
antimalarial, anthelmintic, antitumor, growth regulation,
and antitubercular activities.
I will outline new methods that allow efficient preparation of
new classes of organic peroxides. In particular, I will disclose
the utility of BF3 -catalyzed H2O2-mediated cyclizations
that transform a variety of acyclic precursors, β-ketoesters
and their silyl enol ethers, alkyl enol ethers, enol acetates,
and cyclic acetals into β-hydroperoxy-β-peroxylactones.
The mild reduction of the respective β-hydroperoxy-β-
peroxylactones opened access to previously elusive cyclic
Criegee intermediates of Baeyer-Villiger reaction as stable
β-hydroxy-β-peroxylactones. Despite the great importance of
this >100-year old reaction in organic synthesis and industrial
chemistry, these intermediates have never been isolated and
structurally characterized. β-Peroxylactones, the new class of
organic peroxides, are stable compounds that can be useful
for further synthetic transformations, as well as new targets
for medicinal chemistry and plant protection.
This study was supported by Russian Science Foundation
(Grant № 18-73-00315).
Speaker Biography
Vera A Vil has completed her PhD at the age of 27 at the N. D. Zelinsky
Institute of Organic Chemistry RAS, Russian Federation where she
continues as a research scientist. Her studies focus on oxidational
processes in organic synthesis, medicinal chemistry, and agrochemistry.
She published over 30 publications that have been cited over 400 times
(top 5 papers cited on average >50 times/paper).
e:
Vera A Vil et al., Asian J Biomed Pharmaceut Sci, Volume:9
DOI: 10.4066/2249-622X-C2-020