Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid

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• 作者：J. Stephen Clark ; Carl A. Baxter ; Alexander G. Dossetter ; St&eacute ; phane Poigny ; Jos&eacute ; L. Castro ; William G. Whittingham
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：February 1, 2008
• 年：2008
• 卷：73
• 期：3
• 页码：1040 - 1055
• 全文大小：358K
• 年卷期：v.73,no.3(February 1, 2008)
• ISSN：1520-6904

文摘

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The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesizedusing a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclicether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-formingreactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecularring-opening reaction of an epoxide with a carboxylic acid.