Synthesis of (2′-Methyloxiranyl)quinones as bioreductive alkylating agents

1,4-Benzoquinones and 1,4-naphthoquinones bearing 2′-methyloxiranyl substituents have been synthesized as new bioreductive alkylating agents. The method presented here involved the synthesis of 2-acetyl-1,4-dimethoxybenzenes 6a, b, d and -naphthalenes 6c, e, f , conversion of the acetyl group into 2′-methyloxirane ring using trimethylsulfonium chloride and sodium hydroxide in anhydrous medium, and oxidative demethylation of these intermediates 7a-f to quinones 8a, c, e, f with silver(II) dipicolinate.