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

作者:Qi Chao; Xiong Yuan; Eschenbrenner Lux Vincent; Cong Huan; Porco John A Jr
来源:Journal of the American Chemical Society, 2016, 138(3): 798-801.
DOI:10.1021/jacs.5b12778

摘要

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.

  • 出版日期2016-1-27