Venkateswarlu, R., Kamakshi, C., Subhash, P.V., Moinuddin, S.G.A., Reddy, D. Rama Sekhara, Ward, R.S., Pelter, A., Gelbrich, T., Hursthouse, M.B., Coles, S.J. and Light, M.E. (2006) Transformations of lignans. Part 11: Oxidation of diphyllin with hypervalent iodine reagents and reductive reactions of a resulting 1-methoxy-1-aryl-4-oxonaphthalene lactone. Tetrahedron, 62 (18), 4463-4473. (doi:10.1016/j.tet.2006.02.050).
Abstract
Treatment of diphyllin 4 with phenyliodonium diacetate (PIDA) in methanol affords a 1-methoxy-1-aryl-4-oxonaphthalene lactone 6. Reduction of 6 with lithium aluminium hydride yields, inter alia, 3,4-dihydrodiphyllin 13, while reaction with sodium in ethanol yields 8 as a major product. These reactions illustrate that selective oxidation followed by reduction provides a facile route for the conversion of a 1-arylnaphthalene lactone to novel functionalised naphthalene and dihydronaphthalene derivatives. Of particular interest is that the oxidation indirectly activates the methylene position (C-10) of the ?-lactone, which may then potentially be substituted to give a new series of lignans. Reaction of 6 with hydroxylamine and benzyloxyamine also proceeds by way of initial attack at C-10.
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