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A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-α-methoxybenzyllithiums, which are generated in situ by the treatment of aryl 2-methoxymethylphenyl ketones with lithium diisopropylamide (LDA) in THF at -78 °C, and furan-2(5H)-one to give the corresponding 9-aryl-9-hydroxy-4-methoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one...
2-Acetoxy-1,4-naphthoquinone underwent [2+2] photoaddition to 2-methylpropene, giving a cyclobutanol acetate exclusively. Hydrolysis of the acetate with acid gave the corresponding cyclobutanol, which was stable under the conditions of an alkene-quinone photoaddition; hydrolysis with a base gave a fused 1-indanone derivative. Photolysis of the hypoiodite generated from the cyclobutanol derivative...
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