<i>De novo</i> Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A
Chenlong Zhu, Juntian Zhang, Thomas R. Hoye
Abstract
Here we describe the use of the hexadehydro-Diels–Alder (HDDA) reaction for the de novo construction of the isoindolinone scaffold and its application to the synthesis of the title natural products. The key isoindolinone-forming HDDA reaction involved an unprecedented substrate motif in which an amide carbonyl group was conjugated to the 4π 1,3-diyne component. In addition, a dimethylsilyl (−SiMe2H) substituent was exploited to trigger a Fleming–Tamao–Kumada oxidation for the installation of an essential phenolic hydroxyl group.
Topics & Concepts
ChemistryRing (chemistry)Core (optical fiber)Combinatorial chemistryStereochemistryNatural (archaeology)Organic chemistryComputer scienceArchaeologyTelecommunicationsHistoryCyclization and Aryne ChemistryBioactive Compounds and Antitumor AgentsSynthesis and pharmacology of benzodiazepine derivatives