1: 88 percent / Cs2CO3 / methanol; dimethylformamide / 20 h / 20 °C 2: 81 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C View Scheme

1: Inert atmosphere 2: triethylamine / Inert atmosphere 3: pyridinium chlorochromate / Inert atmosphere View Scheme

1.1: LiN[Si(CH3)3]2 / tetrahydrofuran / -78 °C 1.2: 30 percent / tetrahydrofuran / -78 - 20 °C 2.1: (PhCH2)(Cl)Pd(PPh3)2; LiCl; aq. Na2CO3 / 1,2-dimethoxy-ethane / 86 °C 3.1: 100 percent / H2 / 5 percent Pd/C / ethyl acetate 4.1: aq. LiOH / dioxane / 0 - 20 °C View Scheme

1: 90 percent / DAST / CH2Cl2 / -78 - 20 °C 2: DIBAL-H / tetrahydrofuran / -78 - 20 °C View Scheme

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.5 h / -78 - 0 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 3.33 h / 20 °C / Inert atmosphere 3.1: diethyl ether / 0.25 h / 0 °C / Inert atmosphere 4.1: toluene / 6 h / Inert atmosphere; Reflux 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere 6.1: lithium hydroxide hydrate / tetrahydrofuran / 1.5 h / Inert atmosphere 7.1: pyridine / toluene / 2.5 h / Inert atmosphere; Reflux 8.1: diethyl ether / 0.33 h / 0 °C / Inert atmosphere 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / 20 °C / Inert atmosphere 10.1: Cu(I)CN / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 10.2: 0.75 h / -78 °C / Inert atmosphere 11.1: dimethylsulfide; oxygen; ozone / methanol; dichloromethane / 2 h / -116 - 20 °C / Inert atmosphere 12.1: diethyl ether / 0 °C / Inert atmosphere 13.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 13.2: 1.5 h / -78 - 0 °C / Inert atmosphere 14.1: triethylsilane; tetrakis(triphenylphosphine) palladium(0); lithium chloride / N,N-dimethyl-formamide / 2 h / 55 °C / Inert atmosphere 15.1: lithium hydroxide hydrate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere 16.1: trifluoroacetic acid / tetrahydrofuran; dichloromethane / 10 h / Inert atmosphere View Scheme

1: 85 percent / NaHMDS / tetrahydrofuran / 1.5 h / -78 °C 2: 85 percent / Et3SiH / Pd(PPh3)4 View Scheme

2.1: diethylzinc; trifluoroacetic acid / hexane; dichloromethane / 1 h / -5 °C / Inert atmosphere 2.2: 72 h / -5 - 30 °C / Inert atmosphere 2.3: 24 h / 20 °C 3.1: water; sodium hydroxide / ethanol / 24 h View Scheme

diethylamino-sulfur trifluoride in dichloromethane T=-78 - 20°C; 2.16667 h;

1: 72 percent / DAST / CH2Cl2 / -78 - 20 °C 2: 92 percent / aq. NaOH / tetrahydrofuran / 1 h View Scheme

2.1: diethylzinc; trifluoroacetic acid / hexane; dichloromethane / 1 h / -5 °C / Inert atmosphere 2.2: 72 h / -5 - 30 °C / Inert atmosphere 2.3: 24 h / 20 °C View Scheme