1: With pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride in dichloromethane T=0 - 20°C; 0.333333 h; 2: With ammonium cerium (IV) nitrate in dichloromethane; water T=20°C; 0.25 h; Further stages;

lithium perchlorate in water; acetonitrile T=25°C; anodic oxidation, graphite electrodes, 3V; Yield given;

1: 63 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1.5 h 2: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h 3: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V View Scheme

1: 70 percent / NBS / CHCl3 / 12 h / 25 °C 2: 63 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1.5 h 3: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h 4: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V View Scheme

1: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h 2: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V View Scheme

1: With ammonium cerium(IV) nitrate in acetonitrile T=25°C; 0.25 h; 2: With sodium hydroxide T=25°C; 1 h; Title compound not separated from byproducts;

1.1: zinc / tetrahydrofuran / 2 h / 20 °C / Reflux; Inert atmosphere 1.2: 1.17 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / methanol; water / 2 h / 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine; BOP; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 0 - 20 °C 5.1: pyridine; phosphorus pentachloride / dichloromethane / 8 h / 0 °C 6.1: dichloromethane / 1 h / -30 - -20 °C 7.1: water / dichloromethane / 12 h / 20 °C 8.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 9.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 9.2: 2 h / 20 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 11.1: pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 11.2: 0.25 h / 20 °C View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran 40 h; Ambient temperature;

1.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 2.1: tetrahydrofuran / 0.33 h / -20 °C 3.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 3.2: 8 percent / tetrahydrofuran; hexane / 3 h 4.1: NaBH4 / methanol / 0.33 h / 0 °C 5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 6.2: aq. NaOH / 1 h / 25 °C View Scheme

1.1: 90 percent / aq. NaOH / methanol / 8 h / Heating 2.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 3.1: tetrahydrofuran / 0.33 h / -20 °C 4.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 4.2: 8 percent / tetrahydrofuran; hexane / 3 h 5.1: NaBH4 / methanol / 0.33 h / 0 °C 6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 7.2: aq. NaOH / 1 h / 25 °C View Scheme