Asymmetric synthesis of conformationally constrained 4-hydroxyprolines and their applications to the formal synthesis of (+)-epibatidine
This report describes the synthesis of enantiomerically pure (1S,3S,4R)- and (1S,3R,4R)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, two new conformationally constrained 4-hydroxyprolines, using a straightforward synthetic route and starting from (-)-8-phenylmenthyl 2-acetamidoacrylate....
| Autores: | , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 1999 |
| País: | España |
| Recursos: | Universidad de La Rioja (UR) |
| Repositório: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc6902b750603269e81366 |
| Acesso em linha: | https://investigacion.unirioja.es/documentos/5bbc6902b750603269e81366 |
| Access Level: | Acceso aberto |
| Resumo: | This report describes the synthesis of enantiomerically pure (1S,3S,4R)- and (1S,3R,4R)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, two new conformationally constrained 4-hydroxyprolines, using a straightforward synthetic route and starting from (-)-8-phenylmenthyl 2-acetamidoacrylate. The easy transformation of the pure (1S,3S,4R)-3-hydroxy-7- azabicyclo[2.2.1]heptane-1-carboxylic acid into (1R,4S)-N-Boc-7- azabicyclo[2.2.1]heptan-2-one constitutes a new formal synthesis of (+)- epibatidine. |
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