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Synthesis 2011(3): 443-450  
DOI: 10.1055/s-0030-1258390
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© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of (-)-β-Conhydrine and (+)-α-Conhydrine

Efraim Reyes, Nerea Ruiz, Jose L. Vicario*, Dolores Badía*, Luisa Carrillo
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, P. O. Box 644, 48080 Bilbao, Spain
Fax: +34(94)6012748; e-Mail: dolores.badia@ehu.es; e-Mail: joseluis.vicario@ehu.es;
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Publication History

Received 28 September 2010
Publication Date:
05 January 2011 (online)

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Abstract

We have carried out the stereoselective synthesis of (-)-β-conhydrine and (+)-α-conhydrine, two bioactive α-hydroxyalkyl-substituted piperidines, using the commercially available and inexpensive amino alcohol (S,S)-(+)-pseudoephedrine as chiral auxiliary. The key step of this synthesis relies on new methodology previously developed in our group, consisting of the chemo- and dia­stereoselective addition of Grignard reagents across the C=N bond of α-iminoglyoxylamides derived from (S,S)-(+)-pseudoephedrine followed by the selective monoaddition of organolithium reagents­ to the carbamoyl group, leading to the formation of enantioenriched α-amino ketones.

Key words

asymmetric synthesis - chiral auxiliaries - piperidines - total synthesis - conhydrine