By analogy to the logic of two-phase synthesis, a minimally oxidized macrocyclic intermediate to the portimines was targeted with the assumption that a proper choreography of oxidation events would solve both connectivity and stereochemical issues. The only C-O bonds to be installed at the outset were those residing at C-4 (imine carbon) and C-10 (secondary alcohol). A triple bond on C-7/8 would be a surrogate for the eventual C-7 oxidation and, critically, offer a strategic disconnection to the macrocycle using ringclosing alkyne metathesis (RCAM) . Such a tactic would thereby minimize unstable functional groups and redundant redox manipulations since four key oxidations (C-5, C-13, C-14, C-15) would occur postmacrocyclization. To minimize protecting groups (PGs), the innate reactivity and conformational preferences are utilized via ring-chain reorganization/reconstitution steps. Upon unraveling the macrocycle, the dialkynated precursor traces back to accessible building blocks (Fig. ). Finally, in order to maximize access to useful analogs, a vinyl triflate was selected as a key functionality to be carried through the entire synthesis.