Synthesis of pyrrolizidine alkaloids via 1,3-dipolar cycloaddition involving cyclic nitrones and unsaturated lactones |
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Authors: | Stecko Sebastian Jurczak Margarita Urbańczyk-Lipkowska Zofia Solecka Jolanta Chmielewski Marek |
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Institution: | Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. |
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Abstract: | The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 2,6-dihydroxyhastanecine via reaction sequence involving reduction of the lactone moiety, glycolic cleavage of the terminal diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom. |
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Keywords: | Nitrone Necine bases Iminosugars 1 3-Dipolar cycloaddition |
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