Structural Reassignment of a Marine Metabolite from a Binaphthalenetetrol to a Tetrabrominated Diphenyl Ether

The structure of a reported natural product isolate has
been revised
from (S)-2,2′-dimethoxy-[1,1′-binaphthalene]-5,5′,6,6′-tetraol
to a known tetrabrominated diphenyl ether. After total synthesis of
the reported binaphthalenetetrol was accomplished via a key reduction
of a binaphtho-ortho-quinone, comparison of the physical
properties and NMR spectroscopic data of the synthetic material indicated
that the structure of the natural product isolate was incorrect. Evaluation
of the authentic natural product suggested the structure is a tetrabrominated
diphenyl ether, likely 3,5-dibromo-2-(3,5-dibromo-2-methoxyphenoxy)­phenol.