Photocyclisation of enamides. Part 17. Total synthesis of (±)-corynoline, (±)-12-hydroxycorynoline, and (±)-11-epicorynoline
Abstract
Photocyclisation of the enamide (1) followed by stereoselective functionalisation of the cis-lactam (4c) completed the first total synthesis of the alkaloids, (±)-corynoline (7e), (±)-12-hydroxycorynoline (7d), and (±)-11-epicorynoline (7c). Participation of the basic nitrogen in the oxidation with peracid was also suggested.