Photocyclisation of enamides. Part 22. Syntheses of the despyrrole analogues of some ergot alkaloids including methyl lysergate and isofumigaclavine A2
Abstract
A general synthetic route to the benzo[f]quinolines (21)–(27), the despyrrole analogues of lysergic and isolysergic esters and isofumigaclavine A, is described. The route involves the reductive photo-cyclisation of the enamide (2) followed by glycol formation and oxidative ring opening of the dihydrofuran ring.