De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A

• DOI: 10.1021/acs.orglett.1c02752
• Publication Date: 2021-09-20T13:22:46Z
• Authors: Chenlong Zhu; Juntian Zhang; Thomas R. Hoye
• Keywords: Biological Products; Indoles; Cycloaddition Reaction; Molecular Structure; Phthalimides; Heterocyclic Compounds, 3-Ring; Oxidation-Reduction; 01 natural sciences; 0104 chemical sciences

Here we describe the use of hexadehydro-Diels–Alder (HDDA) reaction for de novo construction isoindolinone scaffold and its application to synthesis title natural products. The key isoindolinone-forming HDDA involved an unprecedented substrate motif in which amide carbonyl group was conjugated 4π 1,3-diyne component. In addition, a dimethylsilyl (−SiMe2H) substituent exploited trigger Fleming–Tamao–Kumada oxidation installation essential phenolic hydroxyl group.