Asymmetric Syntheses of the Flavonoid Diels–Alder Natural Products Sanggenons C and O

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• 作者：Chao Qi ; Yuan Xiong ; Vincent Eschenbrenner-Lux ; Huan Cong ; John A. Porco Jr.
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：January 27, 2016
• 年：2016
• 卷：138
• 期：3
• 页码：798-801
• 全文大小：409K
• ISSN：1520-5126

文摘

Metal-catalyzed, double Claisen rearrangement of a bis-allyloxyflavone has been utilized to enable a concise synthesis of the hydrobenzofuro[3,2-b]chromenone core structure of the natural products sanggenon A and sanggenol F. In addition, catalytic, enantioselective [4+2] cycloadditions of 2′-hydroxychalcones have been accomplished using B(OPh)₃/BINOL complexes. Asymmetric syntheses of the flavonoid Diels–Alder natural products sanggenons C and O have been achieved employing a stereodivergent reaction of a racemic mixture (stereodivergent RRM) involving [4+2] cycloaddition.