Highly Deoxygenated Sugars. II. Synthesis of Chiral Cyclopentenes via Novel Carbocyclization of C-4 Branched Deoxysugars 1

Tri-O-acetyl-d-glucal (1) was converted via Ferrier type II rearrangement with high a-selectivity to 2,3-unsaturated methyl glycosides 2a and 2b using ferric chloride as the catalyst. Palladium induced allylic substitution with sodium tert-butylacetoacetate as a nucleophile leads to C-4 branched sug...

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Bibliographic Details
Published inJournal of carbohydrate chemistry Vol. 22; no. 6; pp. 377 - 383
Main Authors Krohn, Karsten, Gehle, Dietmar, Kamp, Oliver, van Ree, Teunis
Format Journal Article
LanguageEnglish
Published 01.01.2003
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Summary:Tri-O-acetyl-d-glucal (1) was converted via Ferrier type II rearrangement with high a-selectivity to 2,3-unsaturated methyl glycosides 2a and 2b using ferric chloride as the catalyst. Palladium induced allylic substitution with sodium tert-butylacetoacetate as a nucleophile leads to C-4 branched sugars. Subsequent hydrogenation followed by treatment with trifluoroacetic acid affords the highly functionalized chiral cyclopentene derivative 5a as a versatile chiral building block for cyclopentanoids.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
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ISSN:0732-8303
DOI:10.1081/CAR-120025324