Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucineâ
B from (-)-Strychnine.
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 (-)-strychnogucineâ
B (3) from (-)-strychnine (4) is reported. Key steps included (1)â
the Polonovski-Potier activation of strychnine N-oxide; (2)â
a biomimetic Mannich coupling to forge the signature C23-C5' bond that joins two monoterpene indole monomers; and (3)â
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.
Palabras clave
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