Synthesis 2018; 50(15): 2878-2886
DOI: 10.1055/s-0037-1610089
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© Georg Thieme Verlag Stuttgart · New York

Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid

Julio Romero-Ibañez
Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP), 14 Sur Esq. San Claudio, Col. San Manuel, 72570 Puebla, México   Email: fernando.sartillo@correo.buap.mx
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Silvano Cruz-Gregorio
Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP), 14 Sur Esq. San Claudio, Col. San Manuel, 72570 Puebla, México   Email: fernando.sartillo@correo.buap.mx
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Leticia Quintero
Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP), 14 Sur Esq. San Claudio, Col. San Manuel, 72570 Puebla, México   Email: fernando.sartillo@correo.buap.mx
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Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP), 14 Sur Esq. San Claudio, Col. San Manuel, 72570 Puebla, México   Email: fernando.sartillo@correo.buap.mx
› Author Affiliations
Financial support was provided by CONACyT (project number: 255891) and the Marcos Moshinsky Foundation and BUAP-VIEP.
Further Information

Publication History

Received: 10 March 2018

Accepted after revision: 11 May 2018

Publication Date:
26 June 2018 (online)

Abstract

An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product), however, optical rotation did not match with both neither the natural and synthetic material.

Supporting Information

 
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