Total synthesis and assignment of the absolute stereochemistry of xanthoangelol J: development of a highly efficient method for Claisen-Schmidt condensation

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• 作者：Dwipen Kakati ; Nabin C. Barua
• 关键词：Chalcone ; Green synthesis ; Xanthoangelol J ; KHSO4 ; Total synthesis
• 刊名：Tetrahedron
• 出版年：21 January, 2014
• 年：2014
• 卷：70
• 期：3
• 页码：637-642
• 全文大小：408 K

文摘

The first total synthesis of cancer chemopreventive terpenyl hydroxychalcone xanthoangelol J isolated from Angelica keiskei was accomplished with asymmetric epoxidation, aromatic C-alkylation and Claisen-Schmidt condensation via enol mode as key steps. The crucial Claisen-Schmidt condensation has been accomplished by a novel green method using KHSO₄-SiO₂ as a recyclable catalyst under microwave activation. The absolute configuration of the molecule was also determined.