Radical addition to levoglucosenone, synthesis of anhydrosugar herbicide analogues

Abstract Addition of alkyl radicals to levoglucosenone (5) gave 4-C-alkyl-1,6-anhydro-3,4-dideoxy-β-d-erythro-hexopyranos-2-uloses 7 in moderate to good yields. The 4-C-phenyl ethyl derivative 7a was converted by reduction and methylation to the methylene isoster 3 of the powerful herbicide 1.