Asymmetric syntheses of the flavonoid Diels-Alder natural products sanggenons C and O
Files
Accepted manuscript
Date
2016-01-27
Authors
Qi, Chao
Xiong, Yuan
Eschenbrenner-Lux, Vincent
Cong, Huan
Porco, John A.
Version
OA Version
Citation
Chao Qi, Yuan Xiong, Vincent Eschenbrenner-Lux, Huan Cong, John A Porco. 2016. "Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.." J Am Chem Soc, Volume 138, Issue 3, pp. 798 - 801.
Abstract
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.