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Ring-contraction vs ring-expansion reactions of spiro-cyclopropanecarboxylated sugars.

Authors :
Ramakrishna B
Sridhar PR
Source :
Organic letters [Org Lett] 2013 Sep 06; Vol. 15 (17), pp. 4474-7. Date of Electronic Publication: 2013 Aug 21.
Publication Year :
2013

Abstract

Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

Details

Language :
English
ISSN :
1523-7052
Volume :
15
Issue :
17
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
23964753
Full Text :
https://doi.org/10.1021/ol402021e