A Nitrone Based Route to Polyhydroxylated Lactams and Piperidines: An Expeditious Synthesis of rac-Fagomine

Fabio Degiorgis; Marco Lombardo; Claudio Trombini

doi:10.1055/s-1997-1345

Synthesis 1997; 1997(11): 1243-1245
DOI: 10.1055/s-1997-1345

short paper

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A Nitrone Based Route to Polyhydroxylated Lactams and Piperidines: An Expeditious Synthesis of rac-Fagomine

Fabio Degiorgis, Marco Lombardo, Claudio Trombini^*

^*Dipartimento di Chimica “G. Ciamician”, Università di Bologna, via Selmi 2, I-40126 Bologna, Italy, Fax +39(51)259456; E-mail: trombini@ciam.unibo.it

Abstract

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The synthetic versatility of tetrahydrofuro[2,3-d]isoxazol-5(2H)-ones, obtained from TMSOTf-promoted addition of 2-trimethyl-silyloxyfuran to nitrones, is demonstrated in a two-step reductive sequence to give the title compounds. The cycloadducts obtained from a glycolaldehyde derived nitrone are first reduced with DIBAH, then hydrogenolyzed in the presence of Pd(OH)₂ to give polyhydroxylated piperidines, including rac-fagomine. Direct hydrogenolysis of the same cycloadducts gives an easy entry to polyhydroxylated lactams.

nitrones - 2-silyloxyfuran - polyhydroxylated piperidines - lactams - rac-fagomine

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