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Synthesis and elaboration of functionalised carbohydrate-derived spiroketals.

Authors :
van Hooft PA
El Oualid F
Overkleeft HS
van der Marel GA
van Boom JH
Leeuwenburgh MA
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2004 May 07; Vol. 2 (9), pp. 1395-403. Date of Electronic Publication: 2004 Apr 05.
Publication Year :
2004

Abstract

The scope of a stereoselective three-step approach for the synthesis of sugar derived spiroketals is presented. The methodology consists of Grignard addition of vinyl- or allylmagnesium bromide to a carbohydrate lactone, followed by K-10 clay mediated glycosidation with a terminal alkenol and subsequent ring-closing metathesis of the resulting diene. The generality of this procedure is demonstrated by the synthesis of various pyranose- and furanose-derived spiroketals, as well as more advanced tricyclic spiroketal derivatives. It is shown that functionalisation of the double bond in the resulting spiroketals leads to fused polycyclic ethers.

Details

Language :
English
ISSN :
1477-0520
Volume :
2
Issue :
9
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
15105932
Full Text :
https://doi.org/10.1039/b401699h