Abstract
Abstract A short synthetic sequence to rac-5‑hydroxy‑6-hydroxymethylpiperidin-2-one, a useful intermediate in the synthesis of polyhydroxylated piperidine alkaloids, was based on the hydroboration/oxidation reaction of a 6-furanyl-1,2,3,4-tetrahydropyridine derivative prepared from δ-valerolactam by a Suzuki–Miyaura reaction of the corresponding enol phosphate. Two subsequent RuO2-catalyzed oxidation steps concluded the synthesis. By this approach, the title lactam was readily obtained in a suitably protected form on the nitrogen and oxygen atoms for its further elaboration. All new compounds were fully characterized by NMR spectroscopy and mass spectrometry.
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