2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite in phosphate buffer; acetonitrile T=40°C; 18 h;

diborane in tetrahydrofuran T=0 - 20°C; 2 h;

1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h 2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 4.1: 78 percent / TEA; DMAP / CH2Cl2 5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 7.1: Raney-Ni; hydrogen / methanol / Heating 8.1: TBAF / tetrahydrofuran View Scheme

1.1: 78 percent / TEA; DMAP / CH2Cl2 2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 3.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 4.1: Raney-Ni; hydrogen / methanol / Heating 5.1: TBAF / tetrahydrofuran View Scheme

1.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 2.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 3.1: 78 percent / TEA; DMAP / CH2Cl2 4.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 5.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 6.1: Raney-Ni; hydrogen / methanol / Heating 7.1: TBAF / tetrahydrofuran View Scheme

1.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 2.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 3.1: Raney-Ni; hydrogen / methanol / Heating 4.1: TBAF / tetrahydrofuran View Scheme

1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h 2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 4.1: 78 percent / TEA; DMAP / CH2Cl2 5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 7.1: Raney-Ni; hydrogen / methanol / Heating 8.1: TBAF / tetrahydrofuran View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 1.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 2.1: Raney-Ni; hydrogen / methanol / Heating 3.1: TBAF / tetrahydrofuran View Scheme

1: Raney-Ni; hydrogen / methanol / Heating 2: TBAF / tetrahydrofuran View Scheme