Journal
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
Volume 30, Issue 3, Pages 436-453Publisher
SOC BRASILEIRA QUIMICA
DOI: 10.21577/0103-5053.20180217
Keywords
bis-Strychnos alkaloids; biomimetic synthesis; sungucine; Mannich
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Funding
- National Science Foundation [CHE-1111558, CHE-1362461, CHE-1665145, CNS-09-58854, DEG-12262]
- CURE grant from the Pennsylvania Department of Health
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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.
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