- Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines
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A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.
- Matassini, Camilla,Mirabella, Stefania,Goti, Andrea,Cardona, Francesca
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- Polyhydroxyamino-piperidine-type iminosugars and pipecolic acid analogues from a D -mannose-derived aldehyde
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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. The synthesis of diversely substituted polyhydroxypiperidines, polyhydroxyaminopiperidines, and trihydroxypipecolic acid derivatives is reported, using Strecker reactions and double reductive aminations, starting from a D-mannose-derived aldehyde. Copyright
- Matassini, Camilla,Mirabella, Stefania,Ferhati, Xhenti,Faggi, Cristina,Robina, Inmaculada,Goti, Andrea,Moreno-Clavijo, Elena,Moreno-Vargas, Antonio J.,Cardona, Francesca
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p. 5419 - 5432
(2014/11/08)
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