Construction of tetracyclic 3-spirooxindole through cross-dehydrogenation of pyridinium: applications in facile synthesis of (±)-corynoxine and (±)-corynoxine B.
J Am Chem Soc
; 136(52): 17962-5, 2014 Dec 31.
Article
em En
| MEDLINE
| ID: mdl-25496352
ABSTRACT
A facile and straightforward method was developed to construct the fused tetracyclic 3-spirooxindole skeleton, which exists widely in natural products. The formation of the tetracyclic 3-spirooxindole structure was achieved through a transition-metal-free intramolecular cross-dehydrogenative coupling of pyridinium, which were formed in situ by the condensation of 3-(2-bromoethyl)indolin-2-one derivatives with 3-substituted pyridines. As examples of the application of this new methodology, two potentially medicinal natural products, (±)-corynoxine and (±)-corynoxine B, were efficiently synthesized in five scalable steps.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Piridinas
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Compostos de Espiro
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Produtos Biológicos
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Hidrogênio
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Indóis
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
China