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dc.contributor.authorMaslivetc, Vladimir A.
dc.contributor.authorTurner, Danielle N.
dc.contributor.authorMcNair, Kimberly N.
dc.contributor.authorFrolova, Liliyan
dc.contributor.authorRogelj, Snezna
dc.contributor.authorMaslivetc, Anna C.
dc.contributor.authorAksenov, Nicolai A.
dc.contributor.authorRubina, Marina
dc.contributor.authorRubin, Michael
dc.date.accessioned2019-10-31T20:11:08Z
dc.date.available2019-10-31T20:11:08Z
dc.date.issued2018-04-26
dc.identifier.citationMaslivetc, V. A., Turner, D. N., McNair, K. N., Frolova, L., Rogelj, S., Maslivetc, A. A., … Rubin, M. (2018). Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7- exo- trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity. The Journal of organic chemistry, 83(10), 5650–5664. doi:10.1021/acs.joc.8b00640en_US
dc.identifier.urihttp://hdl.handle.net/1808/29685
dc.descriptionThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry,copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.8b00640en_US
dc.description.abstractA strain-release-driven, cation-templated intramolecular nucleophilic addition of tethered alkoxides to prochiral cyclopropenes is described. Employment of chiral β- and γ-amino alkoxides allowed for highly diastereoselective assembly of a small series of enantiopure cyclopropane-fused oxazepanones. It was shown that the chiral center at C-4 plays a crucial role in controlling desymmetrization of the cyclopropenyl moiety, instigated by a profound potassium-templated effect. The preliminary biological activities of the new cyclopropane-fused medium heterocycles against Gram-positive bacteria, Gram-negative bacteria, mycobacteria, cancer cells, and fungus were evaluated.en_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsCopyright © 2018 American Chemical Societyen_US
dc.titleDesymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7-exo-trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activityen_US
dc.typeArticleen_US
kusw.kuauthorMaslivetc, Anna A.
kusw.kuauthorMaslivetc, Victor A.
kusw.kuauthorRubina, Marina
kusw.kuauthorRubin, Michael
kusw.kudepartmentChemistryen_US
dc.identifier.doi10.1021/acs.joc.8b00640en_US
dc.identifier.orcidhttps://orcid.org/0000-0003-1673-6365en_US
dc.identifier.orcidhttps://orcid.org/0000-0001-5717-8297en_US
dc.identifier.orcidhttps://orcid.org/0000-0002-7125-9066en_US
dc.identifier.orcidhttps://orcid.org/0000-0002-1668-9311en_US
kusw.oaversionScholarly/refereed, author accepted manuscripten_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.identifier.pmidPMC6693504
dc.rights.accessrightsopenAccessen_US


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