A C3a-hydroxylated furanose synthon for sesquiterpene lactones

A procedure for the stereocontrolled elaboration of a pendant oxirane at C3 of a 1,2-O-isopropylidenated glycofuranose has been developed. Cleavage of the oxirane with a functionalized carbon nucleophile give a C3a-hydroxylated product which is an attractive synthon for sesquiterpene lactones

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of carbohydrate chemistry 1993-03, Vol.12 (2), p.247-262
Hauptverfasser:	Fraser-Reid, B. (Duke University, Durham, NC), Benko, Z.L
Format:	Artikel
Sprache:	eng
Schlagworte:	CARBOHIDRATOS Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry CHIMIE Exact sciences and technology GLUCIDE LACTONAS LACTONE Organic chemistry Preparations and properties QUIMICA REACCIONES QUIMICAS REACTION CHIMIQUE SESQUITERPENOIDE SESQUITERPENOS
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Beschreibung
Zusammenfassung:	A procedure for the stereocontrolled elaboration of a pendant oxirane at C3 of a 1,2-O-isopropylidenated glycofuranose has been developed. Cleavage of the oxirane with a functionalized carbon nucleophile give a C3a-hydroxylated product which is an attractive synthon for sesquiterpene lactones
ISSN:	0732-8303 1532-2327
DOI:	10.1080/07328309308021274