NOVEL CARBOCYCLIZATION OF A D-GLUCOSE-DERIVED ALKENE

Cyclopentadiene reacts with a D-glucose-derived hex-3-enose derivative to give norbornene derivatives attached at the 2,3-position of a 1,6-anhydrohexose skeleton; although the bicyclic enone isolevoglucosenone is a plausible intermediate in this reaction, the products actually appear to arise throu...

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Veröffentlicht in:	Journal of the Chemical Society. Chemical communications 1992 (10), p.759-760
Hauptverfasser:	HORTON, D, ROSKI, JP
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Chemistry, Multidisciplinary Exact sciences and technology Organic chemistry Physical Sciences Preparations and properties Science & Technology
Online-Zugang:	Volltext
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Zusammenfassung:	Cyclopentadiene reacts with a D-glucose-derived hex-3-enose derivative to give norbornene derivatives attached at the 2,3-position of a 1,6-anhydrohexose skeleton; although the bicyclic enone isolevoglucosenone is a plausible intermediate in this reaction, the products actually appear to arise through initial cycloaddition to a rearranged acyclic sugar derivative with subsequent generation of the anhydro ring.
ISSN:	0022-4936
DOI:	10.1039/c39920000759