The First Total Synthesis of 2,3,6-Tribromo-4,5-dihydroxybenzyl Methyl Ether (TDB) and Its Antioxidant Activity

Several bromophenols were isolated from Symphyocladia latiuscula (Harvey) Yamada, which is a member of the family Rhodomelaceae.1-4The antioxidant activity, of the methanolic extract of the S. latiuscula, on peroxynitrite (ONOO-) and 1,1 -diphenyl-2-picrylhydrazyl (DPPH) radicals was reported by us.5,6We also isolated 2,3,6-tribromo-4,5dihydroxybenzyl methyl ether (TDB) from this methanolic extract and identified the structure depending on spectroscopic evidence.7The reaction of nitric oxide and superoxide gene rates peroxynitrite, which is a cytotoxicant.Peroxynitrite can oxidize sulfhyryls, lipids, amino acids, and nucleotides.8It was demonstrated that excessive formation of peroxynitrite may cause Alzheimers disease, rheumatoid arthritis, cancer, and atherosclerosis.9