Remote Control of the C‐3–C‐4 Double‐Bond Epoxidation of a Chiral 1,2‐Dihydroquinoline: Application to the Synthesis of (–)‐(R)‐Sumanirole (PNU‐95666E)

A twelve-step synthesis of ()-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1,2-dihydroquinoline bearing an Evans' chiral auxiliary at N-1.