Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine
Andrade, Rodrigo B.
Permanent link to this recordhttp://hdl.handle.net/20.500.12613/65
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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.
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
Citation to related workSociedade Brasileira de Química
Has partJournal of the Brazilian Chemical Society, Vol. 30, Iss. 3
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