Synthesis of a novel polyhydroxylated salicylic acid lactone framework.
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.
Rountree
J S Shane
JS
UCD School of Chemistry and Chemical Biology and Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
Murphy
Paul V
PV
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
D062385:Hydroxybenzoates; D026121:Indole Alkaloids; D007783:Lactones; D012459:Salicylates; D017670:Sodium Compounds; C539049:ovatolide; C524957:sodium hydride; D005947:Glucose; C412605:gamma-resorcylic acid