1026975-98-3Relevant academic research and scientific papers
A nitrone based route to polyhydroxylated lactams and piperidines: An expeditious synthesis of rac-Fagomine
Degiorgis,Lombardo,Trombini
, p. 1243 - 1245 (1997)
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.
