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  • Title: Carbohydrate-derived spiroketals: stereoselective synthesis of di-D-fructose dianhydrides via intramolecular aglycon delivery.
    Author: Rubio EM, Ortiz Mellet C, García Fernández JM.
    Journal: Org Lett; 2003 Mar 20; 5(6):873-6. PubMed ID: 12633094.
    Abstract:
    [reaction: see text] A one-pot synthesis of C(2)-symmetric di-d-fructose dianhydrides having the 1,6,9,13-tetraoxadispiro [4.2.4.2]tetradecane skeleton has been accomplished via intramolecular aglycon delivery from (6 --> 6) xylylene-tethered fructofuranose precursors. The stereochemical outcome of the glycosylation-spiroketalization process is governed by the geometrical constraints imposed by the rigid tetracyclic structure of the final compound.
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