1: DMNT With 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran T=20°C; Reduction; 4 h; 2: (E)-2-bromo-6-methylocta-2,6-diene-1,8-diol With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate in N,N-dimethyl-formamide T=50°C; Suzuki coupling; 2.5 h;

1.1: m-CPBA / CH2Cl2 1.2: HIO4 / tetrahydrofuran; H2O 2.1: t-BuOK; 18-crown-6 / tetrahydrofuran; acetonitrile / 0.5 h / -78 °C 2.2: 85 percent / tetrahydrofuran; acetonitrile / 1 h / -78 °C 3.1: 57 percent / DIBAL-H / CH2Cl2 / 1 h / -78 °C 4.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 4.2: 77 percent / Cs2CO3; PdCl2(dppf); Ph3As / dimethylformamide / 2.5 h / 50 °C View Scheme