title: The sulfinyl moiety as an internal nucleophile. 2. Stereoselective synthesis of (-)-galantinic acid via 1,3-asymmetric induction.
abstract: A stereoselective synthesis of (-)-galantinic acid is disclosed. The key steps include hydrolytic kinetic resolution of a racemic epoxide and regio- and stereoselective heterofunctionalization of an olefin, using a pendant sulfinyl group as the nucleophile. The participation of the sulfinyl group was unambiguously proven by conducting the reaction in the presence of H(2)(18)O.
authors.affiliation: Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. purush101@yahoo.com
authors.forename: Sadagopan
authors.initials: S
authors.lastname: Raghavan
authors.forename: S Ramakrishna
authors.initials: SR
authors.lastname: Reddy
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D001407:Bacillus / Q000737:chemistry; D006157:Guanosine Monophosphate / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry
chemical_list: D000596:Amino Acids; D013454:Sulfoxides; C482143:galantinic acid; D006157:Guanosine Monophosphate