Following Boc deprotection with formic acid, eastern fragment 4 was coupled to the central valine residue to generate 17 in 48% yield. Trityl deprotection of 17 followed by coupling with western fragment 16 gave 18 in 56% yield. Remarkably, the fragment coupling on the C-terminus of the branched asparagine proceeded with no substantial aspartimide-related side reactions (e.g., deamination, dehydration, isomerization). This fragment coupling strategy, conjoining both fragments as equally sized tetra-peptides, is the most convergent approach to the fragment coupling of the iterations evaluated (see Table ). As mentioned above, fragment coupling attempts prior to furan oxidation were non-viable, given the sensitivity of late-stage intermediates to the oxidation conditions. Appendage of the valine unit to the western macrocycle followed by coupling of the eastern macrocycle was comparably successful. A potentially more convergent assembly of the decapeptide featuring introduction to the dipeptide Arg-Phe to the eastern fragment before east-west-fragment coupling was not successful (see Table ). As such, 18 was subjected to ester hydrolysis and subsequent coupling with 19 to arrive at the decapeptide 20. At this point, all that remained was conversion of the bromide to the requisite hydroxyl group, followed by global deprotection to complete the synthesis of 2. The final transformations were accomplished in a one-pot procedure consisting of: (1) Miyaura borylation of the bromide with concomitant deprotection of acid-labile protecting groups, (2) oxidation of the resulting boronic acid to the phenol, (3) hydrogenolysis of the benzyl ester, and (4) removal of the final acetyl protecting group on the indole moiety. This final sequence provided 2 in 55% yield, with 14 steps LLS from commercially available starting materials. Synthetic 2 was found to be spectroscopically and chromatographically identical to an authentic sample of the natural product (see SI).