Synthesis of racemic frenolicin via organochromium and organopalladium intermediates

MF Semmelhack, A Zask

文献索引：Semmelhack,M.F.; Zask,A. Journal of the American Chemical Society, 1983 , vol. 105, p. 2034

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被引用次数: 111

摘要

Abstract: A synthesis of the natural quinone antibiotic frenolicin has been completed. Crucial steps include nucleophilic addition/oxidation with an arene-chromium complex to produce a 2, 3-disubstituted anisole derivative and intramolecular alkoxy-carbonylation of an alkene to form the substituted pyran ring. The palladium-catalyzed alkoxy-carbonylation procedure is shown in models to be effective with disubstituted double bonds, giving stereochemical ...