| Abstract
| - Ruthenium-catalyzed ring rearrangement metathesis (RRM) reactions of stereochemically diverse,differentially protected 4-N-allylacetamidocyclopenten-3,5-diols, prepared by using pyridinium saltphotochemistry, have been explored as part of a program to develop novel routes for the synthesisof polyhydroxylated indolizidines. The RRM reactions, which produce selectively protected 1-acetyl-2-allyl-3-hydroxy-1,2,3,6-tetrahydropyridines, were found to take in high yields and with high levelsof regioselectivity. The significance of RRM reactions of 4-N-allylacetamidocyclopenten-3,5-diolsin the context of polyhydroxylated indolizidine synthesis is demonstrated by an application to theconcise preparation of the potent glycosidase inhibitor, (−)-swainsonine.
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