Journal
JOURNAL OF NATURAL PRODUCTS
Volume 74, Issue 9, Pages 1980-1984Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np200596q
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Funding
- EPSRC
- GSK
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(+/-)-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 synthesis of (+/-)-polysiphenol was achieved in four steps in 70% overall yield. Synthesis of the naturally occurring 5,5'-(ethane-1,2-diyl)bis(3-bromobenzene-1,2-diol) (2) (the likely biogenetic precursor of polysiphenol) and 5,5'-(ethane-1,2-diyl)bis(3,4,6-tribromobenzene-1,2-diol) (9) are also reported. The origins of the regioselectivity in the oxidative coupling are explored.
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