Synthesis of Carbasugars from Aldonolactones: Ritter-Type Epoxide Opening of Polyhydroxylated Aminocyclopentanes

Inge Lundt, Steen Karsk Johansen, Hanne Tøfting Kornø

    Research output: Contribution to journalJournal articleResearchpeer-review


    Using the cis-fused cyclopentane-1,4-lactone, 1(R),5(S)-7(R),8(R)-dihydroxy-2-oxabicyclo[3.3.0]oct-3-one (1), as starting material, 5-deoxycarba-*-L-xylo-hexofuranose (6) together with ?- (12) and ?-1-amino-1,5-dideoxycarba-L-xylo-hexofuranose (16) have been prepared using a number of stereoselective transformations. The key step was the regioselective opening of the epoxide 1(R),5(S)-7(R),8(R)-epoxy-2-oxabicyclo[3.3.0]oct-3-one (4) with different nucleophiles.
    Original languageEnglish
    Pages (from-to)171-177
    Publication statusPublished - 1999

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