copper diacetate; di-μ-acetato-bislt;(3,2,10-η-cis-4-acetoxypinene)palladium(II); oxygen in methanol T=35°C; 13 h; Yield given. Yields of byproduct given;

hydrogen; palladium on activated charcoal

4-(N,N-dimethlyamino)pyridine; oxygen; sodium carbonate; Pd(II)-(1,3-dimesityl-1H,3H-imidazole) carbene in toluene T=80°C; intramolecular Wacker cyclisation; 12 h;

copper diacetate; di-μ-acetato-bislt;(3,2,10-η-cis-4-acetoxypinene)palladium(II); oxygen in methanol T=35°C; 13 h; Yield given. Yields of byproduct given;

1: di-μ-acetato-bis<(3,2,10-η-cis-4-acetoxypinene)palladium(II), Cu(OAc)2, O2 / methanol / 13 h / 35 °C 2: 48 percent / Pd(OCOCF3)(OOBut), ButOOH / benzene / 16 h / 50 °C 3: 70 percent / diethyl ether / 1 h / Ambient temperature 4: 82 percent / SnCl4 / benzene / 0.5 h / 0 °C View Scheme

1: di-μ-acetato-bis<(3,2,10-η-cis-4-acetoxypinene)palladium(II), Cu(OAc)2, O2 / methanol / 13 h / 35 °C 2: 48 percent / Pd(OCOCF3)(OOBut), ButOOH / benzene / 16 h / 50 °C 3: BunLi, <Ph3PMe>+Br- / 1) Et2O, hexane, r.t., 4 h, 2) Et2O, 40 deg C, 19 h View Scheme