An indole synthesis via ring expansion of benzocyclobutenone oxime sulfonate was developed. Utility of the indole synthesis was demonstrated by the total synthesis of (+)-CC-1065. The middle and right segments were constructed by a sequential ring expansion of the symmetrical benzo-bis-cyclobutenone. The left segment was also constructed via ring expansion of the methyl-substituted benzocyclobutenone oxime sulfonates. After condensation of these three segments, the dienone cyclopropane structure was formed to complete the total synthesis.
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