A nitrone based route to polyhydroxylated lactams and piperidines: An expeditious synthesis of rac-Fagomine

Article abstract of DOI:10.1055/s-1997-1345

The synthetic versatility of tetrahydrofuro[2,3-d]isoxazol-5(2H)ones, obtained from TMSOTf-promoted addition of 2-trimethylsilyloxyfuran 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.