Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine

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 monom...

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Published inJournal of the Brazilian Chemical Society Vol. 30; no. 3; pp. 436 - 453
Main Authors Zhao, Senzhi, Teijaro, Christiana, Chen, Heng, Sirasani, Gopal, Vaddypally, Shivaiah, O’Sullivan, Owen, Zdilla, Michael, Dobereiner, Graham, Andrade, Rodrigo
Format Journal Article
LanguageEnglish
Published Sociedade Brasileira de Química 01.03.2019
Subjects
CHEMISTRY, MULTIDISCIPLINARY
sungucine
bis-Strychnos alkaloids
biomimetic synthesis
Mannich
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Summary: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.
ISSN:0103-5053
1678-4790
1678-4790
DOI:10.21577/0103-5053.20180217