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Synthesis of the Potential Mannosidase Inhibitor via 1,3-Dipolar Cycloaddition Involving Cyclic Nitrone and Unsaturated Chiral gamma-Lactone

Stecko S., Paśniczek , K., Jurczak M., Solecka J., Chmielewski M.

Polish Journal of Chemistry

2009

Vol. 83, nr 2

237-243

The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid with (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 1,2,6,7-tetrahydroxy-2-hydroxymethyl-indolizidine via reaction sequence involving protection of the hydroxymethyl group, reduction of the lactone moiety, protection of the resulting diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom.