dc.contributor.author | Maslivetc, Vladimir A. | |
dc.contributor.author | Turner, Danielle N. | |
dc.contributor.author | McNair, Kimberly N. | |
dc.contributor.author | Frolova, Liliyan | |
dc.contributor.author | Rogelj, Snezna | |
dc.contributor.author | Maslivetc, Anna C. | |
dc.contributor.author | Aksenov, Nicolai A. | |
dc.contributor.author | Rubina, Marina | |
dc.contributor.author | Rubin, Michael | |
dc.date.accessioned | 2019-10-31T20:11:08Z | |
dc.date.available | 2019-10-31T20:11:08Z | |
dc.date.issued | 2018-04-26 | |
dc.identifier.citation | Maslivetc, 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.8b00640 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/29685 | |
dc.description | This 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.8b00640 | en_US |
dc.description.abstract | A 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.publisher | American Chemical Society | en_US |
dc.rights | Copyright © 2018 American Chemical Society | en_US |
dc.title | Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7-exo-trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Maslivetc, Anna A. | |
kusw.kuauthor | Maslivetc, Victor A. | |
kusw.kuauthor | Rubina, Marina | |
kusw.kuauthor | Rubin, Michael | |
kusw.kudepartment | Chemistry | en_US |
dc.identifier.doi | 10.1021/acs.joc.8b00640 | en_US |
dc.identifier.orcid | https://orcid.org/0000-0003-1673-6365 | en_US |
dc.identifier.orcid | https://orcid.org/0000-0001-5717-8297 | en_US |
dc.identifier.orcid | https://orcid.org/0000-0002-7125-9066 | en_US |
dc.identifier.orcid | https://orcid.org/0000-0002-1668-9311 | en_US |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.identifier.pmid | PMC6693504 | |
dc.rights.accessrights | openAccess | en_US |