Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine
dc.creator | Zhao, Senzhi | |
dc.creator | Chen, Heng | |
dc.creator | Sirasani, Gopal | |
dc.creator | Dobereiner, Graham | |
dc.creator | Andrade, Rodrigo B. | |
dc.creator | Teijaro, Christiana | |
dc.creator | Vaddypally, Shivaiah | |
dc.creator | Zdilla, Michael | |
dc.date.accessioned | 2020-04-22T14:17:24Z | |
dc.date.available | 2020-04-22T14:17:24Z | |
dc.date.issued | 2016-06-15 | |
dc.identifier.citation | Zhao, 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.issn | 0947-6539 | |
dc.identifier.doi | http://dx.doi.org/10.34944/dspace/55 | |
dc.identifier.uri | http://hdl.handle.net/20.500.12613/68 | |
dc.description.abstract | The 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.extent | 6 pages | |
dc.language | English | |
dc.language.iso | eng | |
dc.relation.ispartof | Faculty/ Researcher Works | |
dc.relation.haspart | Chemistry - A European Journal, Vol. 22, Iss. 33 | |
dc.relation.hasversion | S. 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.isreferencedby | Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim | |
dc.rights | All Rights Reserved | |
dc.subject | Sungucine | |
dc.subject | Bid-Strychnos alkaloids | |
dc.subject | Polonovski-Potier | |
dc.subject | Biomimetic synthesis | |
dc.subject | Strychnine | |
dc.title | Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine | |
dc.type | Text | |
dc.type.genre | Post-print | |
dc.description.department | Chemistry | |
dc.relation.doi | https://doi.org/10.1002/chem.201602663 | |
dc.ada.note | For Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu | |
dc.description.schoolcollege | Temple University. College of Science and Technology | |
dc.description.sponsor | National Science Foundation (U.S.) | |
dc.creator.orcid | 0000-0001-5375-0241 | |
dc.creator.orcid | 0000-0001-6203-9689 | |
dc.creator.orcid | 0000-0003-0212-2557 | |
dc.creator.orcid | 0000-0001-6885-2021 | |
dc.temple.creator | Zhao, Senzhi | |
dc.temple.creator | Teijaro, Christiana N. | |
dc.temple.creator | Chen, Heng | |
dc.temple.creator | Sirasani, Gopal | |
dc.temple.creator | Vaddypally, Shivaiah | |
dc.temple.creator | Zdilla, Michael J. | |
dc.temple.creator | Dobereiner, Graham E. | |
dc.temple.creator | Andrade, Rodrigo B. | |
refterms.dateFOA | 2020-04-22T14:17:24Z |