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dc.creatorZhao, Senzhi
dc.creatorTeijaro, Christiana
dc.creatorChen, Heng
dc.creatorSirasani, Gopal
dc.creatorVaddypally, Shivaiah
dc.creatorO'Sullivan, Owen
dc.creatorZdilla, Michael
dc.creatorDobereiner, Graham
dc.creatorAndrade, Rodrigo B.
dc.date.accessioned2020-04-22T14:17:23Z
dc.date.available2020-04-22T14:17:23Z
dc.date.issued2019-03
dc.identifier.citationZhao, Senzhi, Teijaro, Christiana N., Chen, Heng, Sirasani, Gopal, Vaddypally, Shivaiah, O'Sullivan, Owen, Zdilla, Michael J., Dobereiner, Graham E., & Andrade, Rodrigo B.. (2019). Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine. Journal of the Brazilian Chemical Society, 30(3), 436-453. https://dx.doi.org/10.21577/0103-5053.20180217
dc.identifier.issn1678-4790
dc.identifier.doihttp://dx.doi.org/10.34944/dspace/52
dc.identifier.urihttp://hdl.handle.net/20.500.12613/65
dc.description.abstractIt was developed a concise synthetic route resulting in the first syntheses of bis-Strychnos alkaloids (-)-sungucine, (-)-isosungucine, and (-)-strychnogucine B from commercially available (-)-strychnine. Employing a highly convergent synthetic strategy, it was demonstrated that both Strychnos monomers could be efficiently prepared from commercially available (-)-strychnine. The venerable Mannich reaction was enlisted to join the two Strychnos monomers in a biomimetic fashion. Subsequent epimerization and olefin isomerization yielded (-)-strychnogucine B. Functional group manipulation transformed (-)-strychnogucine B into (-)-sungucine and (-)-isosungucine. Computational chemistry was employed to rationalize the regiochemical course of key steps en route to the bis-Strychnos targets.
dc.format.extent18 pages
dc.languageEnglish
dc.language.isoeng
dc.relation.ispartofFaculty/ Researcher Works
dc.relation.haspartJournal of the Brazilian Chemical Society, Vol. 30, Iss. 3
dc.relation.isreferencedbySociedade Brasileira de Química
dc.rightsAttribution CC BY
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/deed.en
dc.subjectBis-Strychnos alkaloids
dc.subjectBiomimetic synthesis
dc.subjectSungucine
dc.subjectMannich
dc.titleSynthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine
dc.typeText
dc.type.genreJournal article
dc.description.departmentChemistry
dc.relation.doihttp://dx.doi.org/10.21577/0103-5053.20180217
dc.ada.noteFor Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
dc.description.schoolcollegeTemple University. College of Science and Technology
dc.creator.orcid0000-0001-5375-0241
dc.creator.orcid0000-0001-6203-9689
dc.creator.orcid0000-0003-0212-2557
dc.creator.orcid0000-0001-6885-2021
dc.temple.creatorZhao, Senzhi
dc.temple.creatorTeijaro, Christiana N.
dc.temple.creatorChen, Heng
dc.temple.creatorSirasani, Gopal
dc.temple.creatorVaddypally, Shivaiah
dc.temple.creatorZdilla, Michael J.
dc.temple.creatorDobereiner, Graham E.
dc.temple.creatorAndrade, Rodrigo B.
refterms.dateFOA2020-04-22T14:17:24Z


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