1: (E)-1-iodo-2-methyl-1-penten-5-ol With tetrakis(triphenylphosphine) palladium(0) in toluene T=0°C; 0.333333 h; Inert atmosphere; 2: vinyl-magnesium bromide in tetrahydrofuran; toluene T=0 - 20°C; 1.5 h; Inert atmosphere;

(Ph3P)PdCl2 in N,N-dimethyl-formamide 18 h; Ambient temperature;

1: 1) CpZrCl2 2) I2 / 1) CH2Cl2, -15 deg C to r.t. 12 h, 2) THF, -30 deg C to r.t., 1 h 2: 76 percent / (Ph3P)PdCl2 / dimethylformamide / 18 h / Ambient temperature View Scheme

Yield given. Multistep reaction;