Macroline-type monoterpenoid indole alkaloids represent a fascinating class of natural products with polycyclic structures, diverse biological and pharmacological activities. Herein the asymmetric total syntheses of two of this type alkaloids, (-)-Alstomicine and (-)-Alstofo-linine A are reported. Notably, these two alkaloids are divergently syn-thesized from a common indole-fused azabicyclo[3.3.1]nonane inter-mediate, which was easily obtained via a Mannich-type cyclization. An SmI2-mediated Reformatsky reaction and a Pd-catalyzed carbonylative lactonization are employed to construct the lactone moieties presented in Alstomicine and Alstofolinine A, respectively.