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The concise synthesis of the novel telomerase inhibitors dictyodendrins B and E was completed in only 9 and 11 steps (longest linear sequence). The highly convergent strategy employed a palladium-catalyzed Larock indole synthesis and a palladium-mediated one-pot consecutive Buchwald-Hartwig amination/C-H activation reaction as key steps. The present synthesis exhibits respectable levels of atom-, redox-, and step-economy.

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A full account of the concise total syntheses of dictyodendrins B and E, and the formal synthesis of dictyodendrin C are described. A palladium‐catalysed Larock indole synthesis was used to form the highly substituted indole core, and a palladium‐mediated one‐pot consecutive Buchwald–Hartwig amination/C–H activation reaction was used to construct the key pyrrolo[2,3‐c]carbazole core. Unsuccessful synthetic strategies are also discussed.

The rhodium(III)-catalyzed intramolecular annulation of alkyne-tethered acetanilides for the synthesis of fused tricyclic indole scaffolds via C-H activation has been developed, which has the potential for the synthesis of many indole alkaloids. This reaction proceeds under mild reaction conditions and with tolerance to a variety of functional groups.