Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine
AUTOR(ES)
Zhao, Senzhi
FONTE
J. Braz. Chem. Soc.
DATA DE PUBLICAÇÃO
2019-03
RESUMO
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.
Documentos Relacionados
- In Vitro Activities of Strychnos Alkaloids and Extracts against Plasmodium falciparum
- Spruceanumines A and B, novel plumeran indole alkaloids from Aspidosperma spruceanum(Apocynaceae)
- Synthesis of New Bis-Iminodihydrofurans
- Regiospecific synthesis of 1,2-bis(azolyl)ethanes
- Pyrrolizidine alkaloids and diterpenes from Villasenoria orcuttii