Total Synthesis of the Marine Metabolite (±)-Polysiphenol via Highly Regioselective Intramolecular Oxidative Coupling

TN Barrett, DC Braddock, A Monta…

Index: Barrett, Tim N.; Braddock, D. Christopher; Monta, Anna; Webb, Michael R.; White, Andrew J.P. Journal of Natural Products, 2011 , vol. 74, # 9 p. 1980 - 1984

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Citation Number: 11

Abstract

(±)-Polysiphenol (1), an atropisomerically stable 4, 5-dibrominated 9, 10- dihydrophenanthrene from Polysiphonia ferulacea, was prepared by a biomimetically inspired highly regioselective intramolecular oxidative coupling of a dibrominated dihydrostilbene. The installation of the two bromine atoms prior to oxidative coupling prevents further oxidation to a planar aromatized phenanthrene. By this strategy, the ...