Loading...
Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine
Zhao, Senzhi Chen, Heng Sirasani, Gopal O'Sullivan, Owen Andrade, Rodrigo B.
Zhao, Senzhi
Chen, Heng
Sirasani, Gopal
O'Sullivan, Owen
Andrade, Rodrigo B.
Citations
Altmetric:
Genre
Journal article
Date
2019-03
Advisor
Committee member
Group
Department
Chemistry
Permanent link to this record
Collections
Research Projects
Organizational Units
Journal Issue
DOI
http://dx.doi.org/10.21577/0103-5053.20180217
Abstract
It 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.
Description
Citation
Zhao, 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
Citation to related work
Sociedade Brasileira de Química
Has part
Journal of the Brazilian Chemical Society, Vol. 30, Iss. 3
ADA compliance
For Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu