1: 2-{4-methoxy-3-(3-methoxypropoxyl)}-phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide in tetrahydrofuran T=63 - 68°C; 4.16667 h; Inert atmosphere; 2: methyl (S)-(4E)-5-chloro-2-isopropyl-4-pentenoate With iron (III) acetylacetonate in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=0 - 5°C; 1 h;

1.1: 4-(N,N-dimethlyamino)pyridine / anhydrous dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 6.2: 1 h / 0 - 5 °C View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C 1.2: pH 2 2.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 3.2: -70 - 5 °C 4.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 5.2: 5.75 h / 0 - 30 °C 6.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 7.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 7.2: 1 h / 0 - 5 °C View Scheme

1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 2.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 5.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 5.2: 1 h / 0 - 5 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 5.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 5.2: 1 h / 0 - 5 °C View Scheme

1.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 6.2: 1 h / 0 - 5 °C View Scheme

1.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 2.2: 5.75 h / 0 - 30 °C 3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 4.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 4.2: 1 h / 0 - 5 °C View Scheme

1.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 1.2: 5.75 h / 0 - 30 °C 2.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 3.2: 1 h / 0 - 5 °C View Scheme

1.1: sulfuric acid / 10.25 h / 0 - 80 °C 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C View Scheme