Synthesis of Tri-O-acetyl-D-allal from Levoglucosenone

Tri-O-acetyl-o-allal has been enantiospecifically synthesized in six steps from levoglucosenone in 55% overall yield. A key step in the synthesis is the anhydro bridge ring-opening with concomitant formation of a 1,3-oxathiolane-2-thione ring.