Methodology for the synthesis of a novel indole based combretastatin A-4 analouge N-Methyl-5,6,7-trimethoxyindole is a viable replacement for the 3,4,5-trimethoxyphenyl moiety within Combretastatin A-4 (CA4). Access to the functionalized indole is achieved via aldol condensation between 3,4,5-trimethoxybenzaldehyde and ethyl-azidoacetate followed by thermolyosis of the resulting vinylazide. Following hydrolysis, decarboxylation and Vilsmeier-Haack formylation of the resulting indole, Corey-Fuchs homologation will complete the the fully elaborated A-ring. A Pd-mediated Sonogashira cross coupling, followed by a boron mediated Z-selective alkyne reduction will complete the synthesis of 1. Our methodology allows for the synthesis of several indole-based CA4. Following completion of the synthesis, in-vitro¬ screening will be utilized to assess the potency of 1 relative to CA4.