β-アシルアクリル酸構造をもつ天然物の合成

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This article describes syntheses of some natural β-acyl acrylates utilizing three newly developed synthetic methods for β-acyl acrylates. The first one includes Lewis acid catalyzed condensation with electrophiles or oxidation of 2- (trialkylsiloxy) furans, followed by hydrolysis. The second one utilizes 1, 3-dipolar cycloaddition of nitrile oxides or silylnitronates to acrylates, and subsequent transformation of the products, 5-alkyloxycarbonylisoxazoles, to β-acyl acrylate. These two methods were applied to the syntheses of 16 - membered lactones, (±) -pyrenophorin and (±) -A 26771B. In the application of the second one, 1, 3-dipolar cycloaddition was used as a new macrocyclic ring closure method. The third one which utilizes oxidative ring cleavage of bicyclic enol ether was applied to the synthesis of 10-membered lactone, pyrenolide B.