1: 92 percent / Amberlyst 15 / 0.5 h / Ambient temperature View Scheme

1: 93 percent / Amberlyst 15 / 0.5 h / 25 °C View Scheme

Yield given. Multistep reaction;

1: 0.9 g / PCC 2: 1.) NaCH2SOCH3 / 1.) THF, 0 deg C, 1 h, 2a.) DMF, -40 deg C, 2 h, 2b.) RT, overnight View Scheme

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -80 °C / |Inert atmosphere 2.2: -80 h / |Inert atmosphere 3.1: lithium borohydride; methanol / diethyl ether / 1.5 h / 0 - 20 °C / |Inert atmosphere 4.1: 2,4,6-trimethyl-pyridine / dichloromethane / 3.5 h / -20 °C / |Inert atmosphere 5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran; toluene / 22 h / 0 - 20 °C 6.1: selenium(IV) oxide; tert.-butylhydroperoxide / 1,2-dichloro-ethane / 3 h / 60 °C 7.1: triethylamine / dichloromethane / 0 - 20 °C / |Inert atmosphere 8.1: trifluoroacetic acid / dichloromethane / 3 h / -20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / |Inert atmosphere 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 20 °C / |Inert atmosphere 11.1: potassium carbonate; methanol / 3 h / 20 °C / |Inert atmosphere 12.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / |Inert atmosphere 13.1: 2-methyl-but-2-ene; sodium dihydrogen phosphate dihydrate; sodium chlorite / water; dichloromethane; tert-butyl alcohol / 18 h / 0 °C 14.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 2 h / 20 °C / |Inert atmosphere 15.1: magnesium; methanol / 3 h / -20 °C / |Inert atmosphere 16.1: caesium carbonate / acetone / 13 h / 0 °C / |Inert atmosphere; |Darkness 17.1: triethylamine; tetrakis(triphenylphosphine) palladium(0); copper(II) sulfate; sodium L-ascorbate / N,N-dimethyl-formamide / 4 h / 80 °C / |Inert atmosphere; |Darkness 18.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C 19.1: C21H27AuNP(1+)*F6Sb(1-) / 1,2-dichloro-ethane / 1 h / 45 °C / |Inert atmosphere 19.2: 0.42 h / 0 °C / |Inert atmosphere 20.1: acetic acid / toluene / 4 h / 80 °C / |Inert atmosphere 21.1: boron trifluoride diethyl etherate; tetrachlorosilane / 1,2-dichloro-ethane / 12 h / 20 °C / |Inert atmosphere 21.2: 10 h / 60 °C / |Inert atmosphere 22.1: caesium carbonate / acetone / 3.5 h / 20 °C / |Inert atmosphere 23.1: silver nitrate; water; triethylamine / acetone / 16 h / 50 °C 24.1: water; lithium hydroxide hydrate / tetrahydrofuran / 20 °C 24.2: -78 - -30 °C View Scheme

in pyridine T=90°C; 24 h;

1: 73 percent / n-Bu3P / tetrahydrofuran / 0.5 h / Ambient temperature 2: 65 percent / Ph3SnH / toluene / 2.5 h / Heating View Scheme

pyridine

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=20°C; 2 h;

1: With lithium aluminium tetrahydride in tetrahydrofuran T=20°C; Inert atmosphere; 2: With water; sodium chloride in tetrahydrofuran Ice water bath;