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Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine.
Zhao, Senzhi; Teijaro, Christiana N; Chen, Heng; Sirasani, Gopal; Vaddypally, Shivaiah; Zdilla, Michael J; Dobereiner, Graham E; Andrade, Rodrigo B.
Afiliación
  • Zhao S; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA.
  • Teijaro CN; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA.
  • Chen H; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA.
  • Sirasani G; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA.
  • Vaddypally S; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA.
  • Zdilla MJ; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA.
  • Dobereiner GE; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA.
  • Andrade RB; Department of Chemistry, Temple University, 1901 N. 13th, St. Philadelphia, Pa, 19122, USA. randrade@temple.edu.
Chemistry ; 22(33): 11593-6, 2016 Aug 08.
Article en En | MEDLINE | ID: mdl-27305659
ABSTRACT
The first chemical syntheses of complex, bis-Strychnos alkaloids (-)-sungucine (1), (-)-isosungucine (2), and (-)-strychnogucine B (3) from (-)-strychnine (4) is reported. Key steps included (1) the Polonovski-Potier activation of strychnine N-oxide; (2) a biomimetic Mannich coupling to forge the signature C23-C5' bond that joins two monoterpene indole monomers; and (3) a sequential HBr/NaBH3 CN-mediated reduction to fashion the ethylidene moieties in 1-3. DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Estricnina / Óxidos N-Cíclicos / Alcaloides Indólicos / Strychnos / Alcaloides / Indoles Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2016 Tipo del documento: Article País de afiliación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Estricnina / Óxidos N-Cíclicos / Alcaloides Indólicos / Strychnos / Alcaloides / Indoles Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2016 Tipo del documento: Article País de afiliación: Estados Unidos