An approach for the enantioselective synthesis of biologically active furanones from a Morita–Baylis–Hillman adduct

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• 作者：Giovanni W. Amarante ; Fern ; o Coelho
• 关键词：Morita&#x2013 ; Baylis&#x2013 ; Hillman ; Furanones ; Palladium ; anti-Inflammatory ; Asymmetric synthesis
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：21 August 2010
• 年：2010
• 卷：66
• 期：34
• 页码：6749-6753
• 全文大小：444 K

文摘

Herein, we disclose an approach for the asymmetric synthesis of both enantiomers of an anti-inflammatory furanone. The approach is based on the utilization of a Morita–Baylis–Hillman adduct as starting material and has as key step a selective epoxide-opening/benzylic oxidation mediated by Palladium (II). This sequence afforded an advanced intermediate, which was used to accomplish the total synthesis. Experimental evidences allowed us to suggest a mechanistic proposal for the oxidation Palladium(II)-mediated.