Sequential Ketene Generation from Dioxane-4,6-dione-keto-dioxinones for the Synthesis of Terpenoid Resorcylates

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• 作者：Daniel C. Elliott ; Tsz-Kan Ma ; Aymane Selmani ; Rosa Cookson ; Philip J. Parsons ; Anthony G. M. Barrett
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：18
• 期：8
• 页码：1800-1803
• 全文大小：329K
• 年卷期：0
• ISSN：1523-7052

文摘

Trapping of the ketene generated from the thermolysis of 2-methyl-2-phenyl-1,3-dioxane-4,6-dione-keto-dioxinone at 50 °C with primary, secondary, or tertiary alcohols gave the corresponding dioxinone β-keto-esters in good yield under neutral conditions. These intermediates were converted by palladium(0)-catalyzed decarboxylative allyl migration and aromatization into the corresponding β-resorcylates. These transformations were applied to the syntheses of the natural products (±)-cannabiorcichromenic and (±)-daurichromenic acid.