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 |
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Authors: | R Venkateswarlu C Kamakshi SGA Moinuddin D Rama Sekhara Reddy A Pelter MB Hursthouse ME Light |
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Institution: | a Department of Organic Chemistry, Andhra University, Visakhapatnam 530 003, India b Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea SA2 8PP, UK c EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Southampton SO17 1BJ, UK |
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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 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. |
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Keywords: | Lignans Oxidative nucleophilic substitutions Diphyllin Synthesis 3 4-Dihydrodiphyllin Oxazinone Benzyloxyoxime |
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