1,3-Dipolar cycloaddition reaction of a d-galactose derived nitrone with allyl alcohol: synthesis of polyhydroxylated perhydroazaazulene alkaloids |
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Institution: | 1. Department of Chemistry, Garware Research Centre, University of Pune, Pune 411 007, India;2. Centre for Material Characterization, National Chemical Laboratory, Pune 411 008, India |
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Abstract: | Diastereofacial intermolecular 1,3-dipolar cycloaddition of d-galactose derived nitrone with allyl alcohol followed by tosylation afforded, in a 1:1 ratio endo- and exo-isooxazolidines 4a and 4b with complete diastereoselectivity at the nitrone carbon. The N–O bond reductive cleavage and SN2 displacement afforded the pyrrolidine ring with a galactose appendage that on acetonide cleavage and reductive amino-cyclization afforded pentahydroxylated perhydroazaazulenes 1a and 1b. |
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