Oxidation of Isomuellitol and Hexahydromuellitol With Chromium Trioxide

Abstract

Chromate oxidation of isomuellitol (2) led cleanly to the production of a cyclic trione , 2,2,9,9,15,15-hexamethyl- 1,8,14-trioxatrispiro [4.1.4.1.4.l]octadecane-6,12,18-trione (4), but the product derived from hexahydromuellitol (3) was an unexpected γ-lactone, 4-hydroxy-2,4-bis(3′-methylbutyl )-3-(4″-methyl-1″-oxopentyloxy)-5-oxotetrahydrofuran-2-carboxylic acid (5).