Ring-rearrangement metathesis of substituted dihydropyrans and dihydrofurans

The rearrangement of dihydropyrans and dihydrofurans featuring appending olefins has been studied. The rearranged products bear resemblance with polyunsaturated di- and trisaccharides. Examples of functionalization prior to, or following, rearrangement are provided suggesting that the method should...

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Bibliographic Details
Published in:Tetrahedron 2011-01, Vol.67 (2), p.339-357
Main Authors: Donnard, Morgan, Tschamber, Théophile, Le Nouën, Didier, Desrat, Sandy, Hinsinger, Karen, Eustache, Jacques
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemical Sciences
Chemistry
Dihydrofurans
Dihydropyrans
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Metathesis
Organic chemistry
Preparations and properties
Ring-rearrangement
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Summary:The rearrangement of dihydropyrans and dihydrofurans featuring appending olefins has been studied. The rearranged products bear resemblance with polyunsaturated di- and trisaccharides. Examples of functionalization prior to, or following, rearrangement are provided suggesting that the method should be useful for the synthesis of nonclassical saccharides. This work also illustrates the power of cascade methatetic processes for increasing molecular complexity starting from relatively simple heterocycles. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.11.036