Stereoselective approach to hydroxyindolizidines: protection/deprotection of the nitrone functionality via cycloaddition/retrocycloaddition.
Org Lett
; 2(16): 2475-7, 2000 Aug 10.
Article
em En
| MEDLINE
| ID: mdl-10956525
ABSTRACT
The enantiomerically pure indolizidine (-)-21 has been synthesized starting from L-malic acid. The key intermediate 20 has been assembled through an intramolecular 1,3-dipolar cycloaddition of a nitrone generated in situ by retrocycloaddition from isoxazolidine 17 or 18. The configuration of the new three stereocenters was set up with complete control in the cycloaddition step. The presented synthetic route provides a general and highly selective methodology toward indolizidines having the [1,8a]-cis configuration.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Indolizinas
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2000
Tipo de documento:
Article
País de afiliação:
Itália