1: With triethylamine in dichloromethane T=0 - 23°C; Inert atmosphere; 2: With methanesulfonyl chloride in dichloromethane T=0 - 23°C; 5 h; Inert atmosphere;

potassium acetate; 18-crown-6 ether in 1,2,2-trifluoro-trichloroethane Ambient temperature;

CyPF-tBu; [Pd(η3-1-Ph-allyl)(μ-Cl)]2; potassium tert-butylate; hydrazine hydrate in 1,4-dioxane T=90°C; 1 h; Inert atmosphere;

hydrazine hydrate; acetic acid in ethanol 15 h; Heating;

1: 1.) EtMgBr / 1.) Et2O, 2 h, reflux; 2.) Et2O, 30 min 2: 1.) BH3*SMe2, 2.) CH3OH / 1.) THF, 0 deg C, 2 h; r.t., 2 h, 2.) THF, 1 h, reflux 3: 80 percent / O3/O2 / ethyl acetate / 14 h 4: 67 percent / 5M HCl / ethanol / 3 h / Heating 5: 1.) NaNO2, 10M HCl, 2.) NaN3 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 10 min 6: 75 percent / NH2NH2*H2O, CH3COOH / ethanol / 15 h / Heating View Scheme

1: 80 percent / O3/O2 / ethyl acetate / 14 h 2: 67 percent / 5M HCl / ethanol / 3 h / Heating 3: 1.) NaNO2, 10M HCl, 2.) NaN3 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 10 min 4: 75 percent / NH2NH2*H2O, CH3COOH / ethanol / 15 h / Heating View Scheme

1: 1.) BH3*SMe2, 2.) CH3OH / 1.) THF, 0 deg C, 2 h; r.t., 2 h, 2.) THF, 1 h, reflux 2: 80 percent / O3/O2 / ethyl acetate / 14 h 3: 67 percent / 5M HCl / ethanol / 3 h / Heating 4: 1.) NaNO2, 10M HCl, 2.) NaN3 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 10 min 5: 75 percent / NH2NH2*H2O, CH3COOH / ethanol / 15 h / Heating View Scheme

1: 1.) NaNO2, 10M HCl, 2.) NaN3 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 10 min 2: 75 percent / NH2NH2*H2O, CH3COOH / ethanol / 15 h / Heating View Scheme

1: 67 percent / 5M HCl / ethanol / 3 h / Heating 2: 1.) NaNO2, 10M HCl, 2.) NaN3 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 10 min 3: 75 percent / NH2NH2*H2O, CH3COOH / ethanol / 15 h / Heating View Scheme

1: 1.) EtMgBr / 1.) Et2O, 2 h, reflux; 2.) Et2O, 30 min 2: 1.) BH3*SMe2, 2.) CH3OH / 1.) THF, 0 deg C, 2 h; r.t., 2 h, 2.) THF, 1 h, reflux 3: 80 percent / O3/O2 / ethyl acetate / 14 h 4: 67 percent / 5M HCl / ethanol / 3 h / Heating 5: 1.) NaNO2, 10M HCl, 2.) NaN3 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 10 min 6: 75 percent / NH2NH2*H2O, CH3COOH / ethanol / 15 h / Heating View Scheme