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A tandem gold(I)-catalyzed rearrangement/Nazarov reaction of enynyl acetates which efficiently provides cyclopenta[b]indol-1-ones as useful precursors for the synthesis of natural and bioactive compounds is described. The synthetic potential of the methodology is demonstrated by the first total synthesis of bruceolline H.

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Construction of Cyclopenta[<i>b</i>]indol-1-ones by a Tandem Gold(I)-Catalyzed Rearrangement/Nazarov Reaction and Application to the Synthesis of Bruceolline H

Construction of Cyclopenta[b]indol-1-ones by a Tandem Gold(I)-Catalyzed Rearrangement/Nazarov Reaction and Application to the Synthesis of Bruceolline H