Total Synthesis of the Marine Natural Product Solomonamide B Necessitates Stereochemical Revision

The first total synthesis of the
proposed structure of solomonamide
B has been achieved. However, the 1H and 13C
NMR spectral data of the synthesized compound was not exactly matching
with that of the natural solomonamide B. This prompted us to revise
the originally proposed structure, in particular, the stereochemistry
of the nonpeptide part, which was confirmed by its total synthesis.
During the course of the synthesis, we have developed an interesting
hydroxy group directed Wacker oxidation of internal olefins in a macrocyclic
setting.