Photocyclisation of enamides. Part 18. Syntheses of the basic structures of chelidonine and related alkaloids
Abstract
Oxidation of the didehydro lactam (6b), prepared by regiospecific photocyclisation of the o-methoxy-substituted enamide (7), with lead tetra-acetate gave exclusively the 12-acetoxy lactam (8b) which was subjected to further oxidation and reduction to develop a general and potential synthetic route for the total synthesis of the chelidonine group of alkaloids.