title: Synthesis of a novel polyhydroxylated salicylic acid lactone framework.
abstract: The facile preparation of a novel 8-membered polyhydroxylated salicylic acid lactone from 2,6-dihydroxybenzoic acid and sodium thio-D-glucose is described. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess TMSCl, which led to isolation of the "natural product like" lactone.
authors.affiliation: UCD School of Chemistry and Chemical Biology and Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: J S Shane
authors.initials: JS
authors.lastname: Rountree
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D002384:Catalysis; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry; D062385:Hydroxybenzoates / Q000737:chemistry; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012459:Salicylates / Q000138:chemical synthesis* / Q000737:chemistry; D017670:Sodium Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D062385:Hydroxybenzoates; D026121:Indole Alkaloids; D007783:Lactones; D012459:Salicylates; D017670:Sodium Compounds; C539049:ovatolide; C524957:sodium hydride; D005947:Glucose; C412605:gamma-resorcylic acid