Comprehensive Summary

Different novel fused multicyclic iminosugars were synthesized from D-ribose tosylate, aniline and vinyl ethyl ether by one-pot three-component stereoselective [4+2] reaction at different temperatures. The iminium-ion is the key intermediate for the reaction. As a result, several complex fused iminosugars 3a were obtained by aza-Diels-Alder mechanism at 60 ^oC, while a series of aza-C-glycosides 5a were prepared by Mannich reaction at room temperature accompanied by another tetrahydroquinoline-fused iminosugars 4a (tricyclic derivatives) through aza-Diels-Alder cycloaddition. This strategy will help to construct structurally diverse and bioactive iminosugar analogues.

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