A general strategy for the synthesis of diversely substituted 3,4,5-trihydroxypiperidines (including two natural products), 5-amino-3,4-dihydroxypiperidines, 3,4,5-trihydroxypipecolic acids, and 2-(aminomethyl)-3,4,5-trihydroxypiperidines is reported. The procedure used a double reductive amination or a Strecker reaction, starting from differently protected aldehydes readily synthesized on a gram scale from D-mannose. The biological activities of the target compounds were evaluated, and some of them showed moderate inhibition of α-L-fucosidase and β-glucosidase.

Polyhydroxyamino-Piperidine-Type Iminosugars and Pipecolic Acid Analogues from a D-Mannose-Derived Aldehyde / Camilla Matassini; Stefania Mirabella; Xhenti Ferhati; Cristina Faggi; Inmaculada Robina; Andrea Goti; Elena Moreno-Clavijo; Antonio J. Moreno-Vargas; Francesca Cardona. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - (2014), pp. 5419-5432. [10.1002/ejoc.201402427]

Polyhydroxyamino-Piperidine-Type Iminosugars and Pipecolic Acid Analogues from a D-Mannose-Derived Aldehyde

MATASSINI, CAMILLA;MIRABELLA, STEFANIA;FAGGI, CRISTINA;GOTI, ANDREA;CARDONA, FRANCESCA
2014

Abstract

A general strategy for the synthesis of diversely substituted 3,4,5-trihydroxypiperidines (including two natural products), 5-amino-3,4-dihydroxypiperidines, 3,4,5-trihydroxypipecolic acids, and 2-(aminomethyl)-3,4,5-trihydroxypiperidines is reported. The procedure used a double reductive amination or a Strecker reaction, starting from differently protected aldehydes readily synthesized on a gram scale from D-mannose. The biological activities of the target compounds were evaluated, and some of them showed moderate inhibition of α-L-fucosidase and β-glucosidase.
2014
5419
5432
Camilla Matassini; Stefania Mirabella; Xhenti Ferhati; Cristina Faggi; Inmaculada Robina; Andrea Goti; Elena Moreno-Clavijo; Antonio J. Moreno-Vargas; Francesca Cardona
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/872839
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