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.
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Erin E
EE
Podlesny
Marisa C
MC
Kozlowski
D001688:Biological Products / Q000737:chemistry*; D018360:Crystallography, X-Ray; D055768:Halogenated Diphenyl Ethers / Q000737:chemistry*; D008386:Marine Biology; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
C574852:3,5-dibromo-2-(3,5-dibromo-2-methoxyphenoxy)phenol; D001688:Biological Products; D055768:Halogenated Diphenyl Ethers