Highly efficient and stereocontrolled oxidative coupling of tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and (+)-WIN 64745

Abstract

The highly efficient and stereocontrolled dimerization of 1,2,3,8-tetrahydropyrrolo[2,3-b]indoles was successfully developed with I₂ as the oxidant, which allowed the rapid synthesis of meso- and rac-chimonanthines, (+)-WIN 64821 and (+)-WIN 64745 in the highest overall yields to date via the oxidation–oxidation–reduction sequence.