New synthesis of all four 1-amino-2-hydroxycyclohexanecarboxylic acids
- Avenoza, A. 1
- Barriobero, J.I. 1
- Cativiela, C. 2
- Fernández-Recio, M.A. 1
- Peregrina, J.M. 1
- Rodríguez, F. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0040-4020
Année de publication: 2001
Volumen: 57
Número: 14
Pages: 2745-2755
Type: Article
D'autres publications dans: Tetrahedron
Résumé
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.