Abstract The total synthesis of quebrachamine was achieved through the macrolactamization of cis-2-alkenylated indole 17, which was prepared by a Sonogashira reaction between indole 5b and piperidine 11 followed by cis-hydrogenation. We found that stoichiometric copper (I) iodide limited the undesired Glaser-type homocoupling of alkyne 11 that would otherwise take place during the Sonogashira coupling. This direct approach ...
