A Novel Approach Towards cis-and trans-Fused Pyranopyrans Based on Ring-Closing Metathesis Reaction of Carbohydrate Derivatives. -Ring-closing metathesis of glycal-derived dienes such as (V) and (X) results in a novel synthesis of both cis-and trans-fused pyranopyrans. Their isomerization at the al
A Flexible Synthesis of Cyclopentitol Derivatives Based on Ring-Closing Metathesis of Carbohydrate-Derived 1,6-Dienes.
β Scribed by Huib Ovaa; Bas Lastdrager; Jeroen D. C. Codee; Gijs A. van der Marel; Herman S. Overkleeft; Jacques H. van Boom
- Book ID
- 101946659
- Publisher
- John Wiley and Sons
- Year
- 2003
- Weight
- 181 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0931-7597
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A general approach towards the construction of highly functionalised pyranopyran and pyranofln-an systems via Grubbs [I~] catalysed ring-closing metatheses of neighbouring vinyl-O-allyl and vinyl-O-protmrgyl functions on monosaeeharide scaffolds is desen'bed.
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The synthesis of the ketoglycosidic enynes 5, 7 and 8 starting from 2,3,4,6-tetra-O-benzyl-D-glucopyranolactone ( 2) is described. These enynes are subjected to ruthenium-mediated