Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, Sichuan University , Chengdu 610041, P. R. China.
J Org Chem. 2018 Jan 19;83(2):754-764. doi: 10.1021/acs.joc.7b02747. Epub 2018 Jan 10.
The formal total syntheses of (-)-actinophyllic acid and its enantiomer starting from the same chiral intermediate are reported. The synthesis features a photoredox organocatalytic asymmetric alkylation to generate the original C15 chirality, a photocatalytic C-H functionalization of 3-methylindole in flow for constructing the C16 all-carbon quaternary center, a regioselective 1,3-dipolar cycloaddition, and an intramolecular Henry reaction to assemble the pentacyclic core of the target molecule.
本文报道了从相同手性中间体出发，（-）-actinophyllic 酸及其对映体的全合成。该合成方法具有光氧化还原有机催化不对称烷基化反应生成原始 C15 手性、在流动相中光催化 3-甲基吲哚的 C-H 官能化反应构建 C16 全碳季碳原子、区域选择性 1,3-偶极环加成反应和分子内 Henry 反应等特点，可用于构建目标分子的五环核心。
