Synthesis and elaboration of functionalised carbohydrate-derived spiroketals |
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Authors: | van Hooft Peter A V El Oualid Farid Overkleeft Herman S van der Marel Gijsbert A van Boom Jacques H Leeuwenburgh Michiel A |
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Affiliation: | TNO Prins Maurits Laboratory, AA Rijswijk, The Netherlands. |
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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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