Abstract
The title indolizidine, a ring-modified analog of the potent mannosidase inhibitor (-)-swainsonine, has been prepared by intramolecular nucleophilic addition of the sp2-type nitrogen atom of a preformed 1,3-oxazine-2-thione heterocycle to the masked aldehyde group in a d-mannose precursor; the stereochemistry of the generated aminoacetalic stereocenter is governed by the generalized anomeric effect, the pseudoanomeric hydroxyl group adopting an axial orientation that mimics that of α-d-mannopyranoside aglycons.
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