Oxidative Furan-to-Indole Rearrangement. Synthesis of 2‑(2-Acylvinyl)indoles and Flinderole C Analogues

Oxidative rearrangement of 2-(2-aminobenzyl)­furans affording 2-(2-acylvinyl)­indoles in a stereocontrolled manner in good-to-excellent yields has been developed. Thus, (2-aminobenzyl)­furans with electron-releasing alkoxy substituents in the phenyl group form only E-isomers of 2-(2-acylvinyl)­indoles. Conversely, substrates without such substituents produce target products as Z-isomers exclusively. A short diastereoselective method for the transformation of the obtained 2-(2-acylvinyl)­indoles into antimalarial bisindole alkaloid flinderole A–C analogues has been developed.