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

DOI: 10.1055/s-1997-1345

Source and publish data:

Synthesis p. 1243 - 1245 (1997)

Update date:2022-08-02

Topics: Piperidines Expeditious synthesis Nitrone

Authors:

Degiorgis

Lombardo

Trombini

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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.

Full text of DOI:10.1055/s-1997-1345

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