N-Acylation of the 3,4-dihydro-1-methylisoquinolines (Ia and b) occurred smoothly to afford the enamides (IIa–k), which underwent ready photocyclisation to give the berbin-8-ones (IVa–d) and (Va–m). Reduction of the berbinones (IVc) and (Vd), (Vh), and (Vj) gave (±)-xylopinine (VIb), (±)-tetrahydropalmatine (VIc), and (±)-sinactine (VId), respectively.
I. Ninomiya, T. Naito and H. Takasugi, J. Chem. Soc., Perkin Trans. 1, 1975, 1720 DOI: 10.1039/P19750001720
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