peracetic acid; sodium acetate in dichloromethane T=7°C; 3.5 h;

1H-imidazole in N,N-dimethyl-formamide T=20°C; 5 h;

silver trifluoroacetate; (2Z,6E)-3-lt;lt;(tert-butyl)dimethylsiloxygt;methylgt;-7-methyl-9-(2',6',6'-trimethylcyclohex-1'-enyl)nona-2,6-dien-1-ol in dichloromethane

1: 95 percent / BuLi / tetrahydrofuran / 12 h / 0 °C 2: 90 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 3: 88 percent / BuLi / diethyl ether / 48 h / 0 °C 4: 90 percent / Raney nickel / ethanol / 6 h / Heating 5: 75 percent / HOOAc, NaOAc / CH2Cl2 / 3.5 h / 7 °C View Scheme

1: 88 percent / BuLi / diethyl ether / 48 h / 0 °C 2: 90 percent / Raney nickel / ethanol / 6 h / Heating 3: 75 percent / HOOAc, NaOAc / CH2Cl2 / 3.5 h / 7 °C View Scheme

1: 90 percent / Raney nickel / ethanol / 6 h / Heating 2: 75 percent / HOOAc, NaOAc / CH2Cl2 / 3.5 h / 7 °C View Scheme

1: 90 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 2: 88 percent / BuLi / diethyl ether / 48 h / 0 °C 3: 90 percent / Raney nickel / ethanol / 6 h / Heating 4: 75 percent / HOOAc, NaOAc / CH2Cl2 / 3.5 h / 7 °C View Scheme

1: 89 percent / Et3N / CH2Cl2 / 4 h / Ambient temperature 2: 81 percent / Ag(CF3COO), (2Z,6E)-3-<<(tert-butyl)dimethylsiloxy>methyl>-7-methyl-9-(2',6',6'-trimethylcyclohex-1'-enyl)nona-2,6-dien-1-ol / CH2Cl2 View Scheme

1: 89 percent / Et3N / CH2Cl2 / 4 h / Ambient temperature 2: 81 percent / Ag(CF3COO), (2Z,6E)-3-<<(tert-butyl)dimethylsiloxy>methyl>-7-methyl-9-(2',6',6'-trimethylcyclohex-1'-enyl)nona-2,6-dien-1-ol / CH2Cl2 View Scheme