title: Stereoselective synthesis of sugar fused β-disubstituted γ-butyro-lactones: C-spiro-glycosides from 1,2-cyclopropanecarboxylated sugars.
abstract: A stereoselective methodology was developed for the construction of C-spiro-glycosides in two steps involving bromonium ion activated solvolytic ring opening of sugar derived 1,2-cyclopropanecarboxylates followed by a one-pot dehydrohalogenation, intramolecular hetero-Michael addition (IHMA) and ester hydrolysis. The obtained spirocyclic lactols were further converted to enantiomerically pure spirolactones.
authors: School of Chemistry, University of Hyderabad, Hyderabad, 500 046, India. prssc@uohyd.ernet.in
authors: Perali Ramu
authors: PR
authors: Sridhar
authors: Kalapati
authors: K
authors: Seshadri
authors: Gadi Madhusudhan
authors: GM
authors: Reddy
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003521:Cyclopropanes / Q000737:chemistry*; D006027:Glycosides; D006868:Hydrolysis; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C438934:C-glycoside; D003521:Cyclopropanes; D006027:Glycosides; D009005:Monosaccharides; D013141:Spiro Compounds; C015766:cyclopropanecarboxylic acid; D015107:4-Butyrolactone