An expedient relay gold(I) and Brønsted acid catalyzed hydroamination/Nazarov cyclization of 1-(2-aminophenyl)pent-4-en-2-ynols for the synthesis of various polyfunctionalized cyclopenta[b]indoles is described. The synthetic utility of this method has been demonstrated by the synthesis of a few unprecedented pentacyclic indoles and indole-steroidal hybrids. Further, the new methodology has been successfully applied to the enantioselective synthesis of core carbon structure of the polyveoline family of natural products.