A series of unexpected semi-saturated fused multicyclic iminosugars were synthesized by one-pot stereoselective three-components reactions of D-ribose tosylate, aniline and cycloketenes at heating condition. The N-aryl enamine derived from iminium-ion is the key intermediate for the reaction. As a result, several novel complex fused iminosugars 3a/4a were obtained through aza hetero Diels-Alder mechanism at 80 oC. This strategy will help to prepare the bioactive iminosugar analogues with structural diversity.
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Xie et al. (2024) studied this question.
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