Attention was then turned to constructing the 14-membered macrocycle in portimines' skeleton through RCAM, a maneuver that might be derailed by the imine, olefins, or vinyl triflate. Fürstner's extremely efficient, canopy-shaped catalyst, [Mo] was chosen at this point due to its outstanding functional compatibility and demonstrated robustness . The pivotal RCAM step could indeed be achieved in 53-65% yield when heated 7 with [Mo] in toluene. However, a relatively high catalyst loading (12.5 mol %) was required, presumably due to the basic imine nitrogen. To lower the catalyst loading, the imine was masked with a Troc group, followed by exposing the formed enamide to 2.0 mol % . In this case, formation of macrocycle 14 was completed in one hour. Treating crude 14 with acidic wet methanol liberated the C-4 ketone and deprotected the TBS ether on C-10, affording 15 as a white powder (68% overall isolated yield over 2 steps, multigram-scale).