SYNTHESIS OF 1,6:3,4-DIANHYDRO-β-D-TALOPYRANOSE FROM LEVOGLUCOSENONE: EPOXIDATION OF OLEFIN VIA trans-IODOACETOXYLATION

Article abstract of DOI:10.3987/COM-92-6112

Levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose, 1) was converted to give 1,6:3,4-dianhydro-β-D-talopyranose (8) in good yield through stereoselective trans-iodoacetoxylation followed by basic hydrolysis.