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R. Venkateswarlu C. Kamakshi S.G.A. Moinuddin D. Rama Sekhara Reddy A. Pelter M.B. Hursthouse M.E. Light 《Tetrahedron》2006,62(18):4463-4473
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 γ-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. 相似文献
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