Synthesis of (±)-lecanindole D

The first synthesis of the racemate of lecanindole D, an indole sesquiterpenoid with potent and selective agonist activity toward the progesterone receptor, has been achieved from a known tetracyclic alcohol by using a diastereoselective installation of its tertiary hydroxy group via an epoxide intermediate and a Pd(II)-mediated construction of the indole ring moiety as the key transformations.