title: Ring-contraction vs ring-expansion reactions of spiro-cyclopropanecarboxylated sugars.
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.
authors: School of Chemistry, University of Hyderabad, Hyderabad-500 046, India.
authors: Bandi
authors: B
authors: Ramakrishna
authors: Perali Ramu
authors: PR
authors: Sridhar
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006031:Glycosylation; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002241:Carbohydrates; D013141:Spiro Compounds; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene