Abstract

Radical ring-opening reactions of bicyclo[4.2.0]octanones, its C6 alkyl derivatives, and tricyclic ketones promoted by SmI 2 gave cyclohexanones via fission of the external cyclobutane bond. The CO 2Me, CN, and phenyl derivatives led to the production of the eight-membered ring compounds through cleavage of the central cyclobutane bond. Using this regioselective reaction, the synthesis of (±)-acorenone was achieved.

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