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Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate

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journal contribution
posted on 12.06.2019 by Taku Imaizumi, Yumi Yamashita, Yuki Nakazawa, Kentaro Okano, Juri Sakata, Hidetoshi Tokuyama
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.