Intramolecular 5-endo-trig aminomercuration of beta-hydroxy-gamma-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues.
J Org Chem
; 71(12): 4667-70, 2006 Jun 09.
Article
en En
| MEDLINE
| ID: mdl-16749803
ABSTRACT
The intramolecular aminomercuration reaction of sugar-derived beta-hydroxy-gamma-alkenylamines 8a-c undergoes 5-endo-trig cyclization in high yield. The sugar-substituted pyrrolidines thus obtained were elaborated to the synthesis of polyhydroxylated indolizidine alkaloids, namely, castanospermine 1a, 1-epi-castanospermine 1b, and 8a-epi-castanospermine 1c, having promising glycosidase inhibitory activities.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Pirrolidinas
/
Indolizinas
Idioma:
En
Revista:
J Org Chem
Año:
2006
Tipo del documento:
Article
País de afiliación:
India