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An efficient, stereoselective, and base-controlled procedure for the preparation of polyhydroxy bicyclic diazenes and polyhydroxy bicyclic hydrazones is described, starting from sugar-derived methyl 6-deoxy-6-iodo-hexosides. The one-pot synthesis involves a three-step reaction, including ring-opening, condensation with tosylhydrazine, and intramolecular cycloaddition with terminal alkene, which affords...
An efficient and stereoselective synthesis of diaza-triquinanes, the skeleton structures of many natural products, has been accomplished by intramolecular 1,3-dipolar cycloaddition of azomethine imine generated from sugar-derived hex-5-enal and pyrazolidin-3-one.
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