Liu, Xiaojing Jia, Junhao Jia, Yuanliang Gu, He Luo, Jingwen Chen, Xiaochuan A Flexible and Divergent Strategy to Flavonoids with a Chiral A‑Ring Featuring Intramolecular Michael Addition: Stereoselective Synthesis of (+)-Cryptocaryone, (+)-Cryptogione F, and (+)-Cryptocaryanones A and B, as Well as (+)-Cryptochinones A and C A flexible strategy has been developed to synthesize divergent flavonoids bearing a chiral A-ring. As two key steps, the coupling via a boron-mediated aldol condensation and the cyclization via a highly stereoselective intramolecular Michael addition of 1,3-diketone proceed under mild conditions; thus, the chiral flavonoids bearing C-7 oxy functional groups or olefinic bonds are both easily accessible. Using this approach, the first synthesis of (+)-cryptogione F, (+)-cryptocaryanone B, and (+)-cryptochinones A and C, as well as stereoselective synthesis of (+)-cryptocaryone and (+)-cryptocaryanone A, were achieved from 2-deoxy-d-ribose in high overall yields. cryptogione;chiral flavonoids;Cryptocaryanone;Stereoselective Synthesis;boron-mediated aldol condensation;Flexible;Featuring;C -7 oxy;Flavonoid;cryptocaryone;Cryptocaryone;Cryptochinone;2- deoxy-d-ribose;cyclization;strategy;cryptocaryanone;diketone;chiral A-ring;Intramolecular;approach;Chiral;cryptochinone;yield;stereoselective synthesis;olefinic bonds;stereoselective intramolecular Michael addition;Cryptogione;Divergent Strategy 2018-03-19
    https://acs.figshare.com/articles/journal_contribution/A_Flexible_and_Divergent_Strategy_to_Flavonoids_with_a_Chiral_A_Ring_Featuring_Intramolecular_Michael_Addition_Stereoselective_Synthesis_of_-Cryptocaryone_-Cryptogione_F_and_-Cryptocaryanones_A_and_B_as_Well_as_-Cryptochinones_A_and_C/6000185
10.1021/acs.orglett.8b00479.s001