We presented two methods for the total synthesis of the anion-binding macrocycle cyanostar. The large-scale synthesis provided cyanostar in multigram 12-g quantities with limited byproduct formation over 6 steps and a 2-week duration. The small-scale pathway provided cyanostar in lower yields using 5 steps and can be completed in just 2 days without the purification of intermediates. The cyanostar macrocycle can be made reliably along two different pathways that either prioritize reaction time or overall yield.