1: 6-bromo-2-methylhexanoic acid With 1-methyl-pyrrolidin-2-one; 1,1-dimethylethylmagnesium chloride in tetrahydrofuran T=-78°C; 0.166667 h; Inert atmosphere; 2: n-octylmagnesium chloride With buta-1,3-diene; nickel dichloride in tetrahydrofuran P=760.051 Torr; 1 h; Inert atmosphereCooling with ice;

copper(I) oxide in acetonitrile 12 h; Heating;

1: 85percent KOH / aq. ethanol / Heating 2: 0.5 h / 185 - 190 °C View Scheme

1: 1.) EtONa / 1.) ethanol, reflux, 15 min, 2.) ethanol, reflux, overnight 2: 85percent KOH / aq. ethanol / Heating 3: 0.5 h / 185 - 190 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / dichloromethane / 16 h / -20 - 4 °C / Inert atmosphere 2: sodium tetrahydroborate; acetic acid / 4 °C / Inert atmosphere 3: methanol / Reflux; Inert atmosphere 4: palladium 10 on activated carbon; hydrogen / ethyl acetate / 16 h / 760.05 Torr 5: ethanol; sodium hydroxide / 0.25 h / 50 °C / Inert atmosphere View Scheme

1: methanol / Reflux; Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / ethyl acetate / 16 h / 760.05 Torr 3: ethanol; sodium hydroxide / 0.25 h / 50 °C / Inert atmosphere View Scheme

ethanol; sodium hydroxide T=50°C; 0.25 h; Inert atmosphere;

1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 16 h / 760.05 Torr 2: ethanol; sodium hydroxide / 0.25 h / 50 °C / Inert atmosphere View Scheme

1: sodium tetrahydroborate; acetic acid / 4 °C / Inert atmosphere 2: methanol / Reflux; Inert atmosphere 3: palladium 10 on activated carbon; hydrogen / ethyl acetate / 16 h / 760.05 Torr 4: ethanol; sodium hydroxide / 0.25 h / 50 °C / Inert atmosphere View Scheme

(i) Raney-Ni, THF, (ii) Raney-Ni, (iii) KOH, aq. EtOH; Multistep reaction;