Given the success of the Larock reaction in forging the central ring, this strategy was also pursued as a means to perform the second macrocyclization. This disconnection required installation of an ortho bromoaniline functionality onto the hydroxyl group of 20 with inversion of the stereochemistry. A variety of etherification tactics were evaluated using alkynes derived from both 10 and 11 in order to test both stereoretentive (i.e. SNAr) and stereoinvertive strategies. Ultimately, Mitsunobu displacement of the alcohol with 3-bromo-2-nitrophenol (7) proved to be the most successful. Through extensive reagent and solvent screening (see inset table, step 7), it was revealed that the unusual combination of PMe3 and TMAD in toluene afforded 21 in 60% isolated yield (500 mg scale).