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  • Title: Synthesis and elaboration of functionalised carbohydrate-derived spiroketals.
    Author: van Hooft PA, El Oualid F, Overkleeft HS, van der Marel GA, van Boom JH, Leeuwenburgh MA.
    Journal: Org Biomol Chem; 2004 May 07; 2(9):1395-403. PubMed ID: 15105932.
    Abstract:
    The scope of a stereoselective three-step approach for the synthesis of sugar derived spiroketals is presented. The methodology consists of Grignard addition of vinyl- or allylmagnesium bromide to a carbohydrate lactone, followed by K-10 clay mediated glycosidation with a terminal alkenol and subsequent ring-closing metathesis of the resulting diene. The generality of this procedure is demonstrated by the synthesis of various pyranose- and furanose-derived spiroketals, as well as more advanced tricyclic spiroketal derivatives. It is shown that functionalisation of the double bond in the resulting spiroketals leads to fused polycyclic ethers.
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