New synthesis of all four 1-amino-2-hydroxycyclohexanecarboxylic acids
This report describes a new synthesis of the four stereoisomers of 1-amino-2-hydroxycyclohexanecarboxylic acids [(1S,2S)-, (1R,2R)-, (1S,2R)- and (1R,2S)-c 6Ser], four conformationally constrained serine (Ser) analogues, possessing a six-membered carbocyclic ring. Initially, we synthesised cis-c 6Se...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2001 |
| País: | España |
| Institución: | Universidad de La Rioja (UR) |
| Repositorio: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc6904b750603269e81385 |
| Acceso en línea: | https://investigacion.unirioja.es/documentos/5bbc6904b750603269e81385 |
| Access Level: | acceso abierto |
| Palabra clave: | Amino acids and derivatives Cyclohexanes Diels-Alder reactions Resolution |
| Sumario: | This report describes a new synthesis of the four stereoisomers of 1-amino-2-hydroxycyclohexanecarboxylic acids [(1S,2S)-, (1R,2R)-, (1S,2R)- and (1R,2S)-c 6Ser], four conformationally constrained serine (Ser) analogues, possessing a six-membered carbocyclic ring. Initially, we synthesised cis-c 6Ser and trans-c 6Ser in their racemic forms, using as key steps the Diels-Alder reactions of methyl 2-benzamidoacrylate with Danishefsky's diene and 1-methoxy-1,3-butadiene, respectively. The optically active forms were achieved by resolution methods. © 2001 Elsevier Science Ltd. |
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