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Dearomatization of indoles has been a powerful and potentially versatile strategy to construct many unprecedented complex alkaloids from structurally simple substrates.1 The first dearomative indole [5+2] cycloaddition reaction with an oxidopyrylium ylide resulted in efficient and diastereoselective construction of some highly functionalized and synthetically challenging oxa-cyclohepta[b]indoles.The protocol notably proceeded under very mild conditions enabling high functional-group tolerance and unique endo-selectivity.2