In this account, recent progress on the synthetic studies of several monoterpene indole alkaloids, (±)-mersicarpine, misassigned (±)-tronoharine, and (±)-leuconodines D and E, is summarized. Specifically, the rationale for the design and development of the Lewis acid catalyzed S N1-type substitution and formal [3+3] cycloaddition reaction of indol-2-yl carbinols, and the Pd-catalyzed aerobic oxidative intramolecular Heck cross-coupling of indolyl amides tethered with a terminal olefin functionality, are emphasized. These key reactions set the basis for the rapid construction of the fused ring skeleton containing an all-carbon quaternary center at the indol-2-yl position. 1 Introduction 2 Synthetic Study of (±)-Mersicarpine 3 Synthetic Study of the Misassigned (±)-Tronoharine 4 Study of the Asymmetric Reaction of Indol-2-yl Carbinols 5 Synthetic Study of (±)-Leuconodines D and E 6 Conclusion. © 2021 Georg Thieme Verlag. All rights reserved.