An evolution of a synthetic route leading to a successfulenantioselectivetotal synthesis of monoterpenoid indole alkaloid (+)-alstonlarsineA is represented. The unique 9-azatricyclo[4.3.1.0(3,8)]decanecore was assembled through an efficient domino sequence comprisingenamine formation in situ, followed by intramolecular dearomativeinverse-electron-demand Diels Alder reaction. The preparation of thetricyclic dihydrocyclohepta[b]indole key intermediatevia the intramolecular Horner-Wadsworth-Emmons reactionrequired a development of a new general method for the introductionof the phosphonoacetate moiety into the indole C-2 position, throughcopper-carbenoid insertion. The modular nature of the representedsynthetic approach makes it suitable for the synthesis of analogueswith different substituents' patterns.