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dc.creatorZhao, Senzhi
dc.creatorChen, Heng
dc.creatorSirasani, Gopal
dc.creatorDobereiner, Graham
dc.creatorAndrade, Rodrigo B.
dc.creatorTeijaro, Christiana
dc.creatorVaddypally, Shivaiah
dc.creatorZdilla, Michael
dc.date.accessioned2020-04-22T14:17:24Z
dc.date.available2020-04-22T14:17:24Z
dc.date.issued2016-06-15
dc.identifier.citationZhao, Senzhi; Teijaro, Christiana N.; Chen, Heng; Sirasani, Gopal; Vaddypally, Shivaiah; Zdilla, Michael J.; Dobereiner, Graham E.; Andrade, Rodrigo B. (2016): Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine. Postprint. 10.1002/chem.201602663.
dc.identifier.issn0947-6539
dc.identifier.doihttp://dx.doi.org/10.34944/dspace/55
dc.identifier.urihttp://hdl.handle.net/20.500.12613/68
dc.description.abstractThe first chemical syntheses of complex, bis‐Strychnos alkaloids (−)‐sungucine (1), (−)‐isosungucine (2), and (−)‐strychnogucine B (3) from (−)‐strychnine (4) is reported. Key steps included (1) the Polonovski–Potier activation of strychnine N‐oxide; (2) a biomimetic Mannich coupling to forge the signature C23−C5′ bond that joins two monoterpene indole monomers; and (3) a sequential HBr/NaBH3CN‐mediated reduction to fashion the ethylidene moieties in 1–3. DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners.
dc.format.extent6 pages
dc.languageEnglish
dc.language.isoeng
dc.relation.ispartofFaculty/ Researcher Works
dc.relation.haspartChemistry - A European Journal, Vol. 22, Iss. 33
dc.relation.hasversionS. Zhao, C. N. Teijaro, H. Chen, G. Sirasani, S. Vaddypally, M. J. Zdilla, G. E. Dobereiner, R. B. Andrade (2016). Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine. Chem. Eur. J., 22, 11593. https://doi.org/10.1002/chem.201602663.
dc.relation.isreferencedbyWiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
dc.rightsAll Rights Reserved
dc.subjectSungucine
dc.subjectBid-Strychnos alkaloids
dc.subjectPolonovski-Potier
dc.subjectBiomimetic synthesis
dc.subjectStrychnine
dc.titleConcise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine
dc.typeText
dc.type.genrePost-print
dc.description.departmentChemistry
dc.relation.doihttps://doi.org/10.1002/chem.201602663
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.description.sponsorNational Science Foundation (U.S.)
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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