Substituent-directed oxidation: a simple preparation of γ and δ-lactones by oxidative cyclization of hydroxyalkenes.

Article abstract of DOI:10.1016/S0040-4039(00)61860-9

Treatment of tertiary γ- and δ-hydroxyalkenes with chromium trioxide in acetic acid/acetic anhydride gives reasonable yields of γ- and δ-lactones by oxidative cyclization, with loss of one carbon. A mechanism is proposed involving formation of a chromate monoester, followed by intramolecular oxidative attack on the alkene.