One-Pot Friedel–Crafts/Robinson–Gabriel Synthesis of the Indole-Oxazole Scaffold and Its Application to the Synthesis of Breitfussins C, G, and H
Evan Savelson, Jetze J. Tepe
Abstract
The indole-oxazole scaffold is found in a range of biologically active natural products, including the breitfussin family. Divergent methods that provide access to the indole-oxazole template are relatively scarce, which impedes the wider exploration of these natural products and their exciting biological activity. Herein, we describe a highly divergent synthesis of the indole-oxazole scaffold via a one-pot Friedel-Crafts/Robinson-Gabriel synthesis and the application of this methodology to the synthesis of breitfussins C, G, and H.
Topics & Concepts
OxazoleIndole testFriedel–Crafts reactionChemistryScaffoldCombinatorial chemistryStereochemistryOrganic chemistryCatalysisComputer scienceDatabaseCarbohydrate Chemistry and SynthesisMicrobial Natural Products and BiosynthesisSynthesis of Indole Derivatives