1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2: cerium(III) chloride / tetrahydrofuran / 0 - 5 °C View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 3.1: water; sodium hydroxide / tetrahydrofuran; methanol / 2 h / 25 - 30 °C 4.1: hydrogenchloride / water / 25 - 30 °C / pH 6.5 - 7 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 5.2: 1.5 h / 0 - 5 °C 6.1: n-butyllithium / tetrahydrofuran; hexane / -15 - 0 °C / Inert atmosphere 6.2: 19 h / -5 - 2 °C / Inert atmosphere 7.1: ethyl acetate / 15 h / 25 - 30 °C / Inert atmosphere 8.1: sulfuric acid; water / 2 h / 0 - 10 °C / Inert atmosphere 9.1: ethyl acetate / 18 h / 25 - 30 °C / Inert atmosphere 10.1: acetic acid / dichloromethane; water / 0.5 h / pH 3.5 - 4 10.2: 0.5 h / 25 - 30 °C View Scheme

1.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / toluene; tetrahydrofuran / 1 h / -15 °C 1.2: 20 °C 2.1: ethyl acetate; hexane / 27 h / 20 °C View Scheme

1: (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-hydroxy-1-methylethyl)-phenyl]-propan-1-ol With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine in tetrahydrofuran T=-15 - -10°C; Inert atmosphere; 2: 1-(mercaptomethyl)-cyclopropaneacetic acid With sodium methylate in tetrahydrofuran; methanol; isobutyl methylketone T=-15 - 20°C;

1: (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-hydroxy-1-methylethyl)-phenyl]-propan-1-ol With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; toluene T=-15°C; 1 h; 2: methyl 2-(2-(sulfanylmethyl)cyclopropyl)acetate With caesium carbonate in tetrahydrofuran; N,N-dimethyl-formamide; toluene T=20°C;

1.1: N-ethyl-N,N-diisopropylamine / toluene; acetonitrile / 40 °C 1.2: 2.5 - 3 h / -27 °C 2.1: sodium methylate / N,N-dimethyl-formamide; methanol / 1.5 h / -10 °C / Inert atmosphere 2.2: 15 h / -5 °C / Inert atmosphere 2.3: 0.17 - 0.25 h View Scheme

1.1: N-ethyl-N,N-diisopropylamine / toluene; acetonitrile / 40 °C 1.2: 2.5 - 3 h / -27 °C 2.1: sodium methylate / N,N-dimethyl-formamide; methanol / 1.5 h / -10 °C / Inert atmosphere 2.2: 15 h / -5 °C / Inert atmosphere 2.3: 0.17 - 0.25 h 3.1: ethyl acetate / 0.5 h / 20 °C 4.1: 2,3-dihydroxybutanedioic acid / dichloromethane; water / 0.25 - 0.33 h 4.2: 0.08 - 0.17 h View Scheme

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C 1.2: 5 h / -25 °C 2.1: sodium methylate / methanol; N,N-dimethyl-formamide / 1 h / -15 °C 2.2: 10 h / -5 - 5 °C 3.1: water; sodium hydroxide / methanol / 3 h / 60 - 65 °C View Scheme