formic acid; triethylamine; palladium diacetate in N,N-dimethyl-formamide T=80°C; 11 h;

Penicillium janthinellum AS; liquid potato medium in acetone T=27°C; 120 h; Microbiological reaction;

1: 89 percent / dioxane / 12 h / 70 °C 2: 68 percent / ZnCl2 / 1.5 h / 90 °C 3: 82 percent / aq. NH4OH; iodine; aq. KI / dioxane / 0.83 h / ice cooling 4: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 80 °C 5: 92 percent / OsO4; 2-methyl-2-propanol; NaIO4 / dioxane; H2O / 2 h / 20 °C 6: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 7: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

1: 68 percent / ZnCl2 / 1.5 h / 90 °C 2: 82 percent / aq. NH4OH; iodine; aq. KI / dioxane / 0.83 h / ice cooling 3: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 80 °C 4: 92 percent / OsO4; 2-methyl-2-propanol; NaIO4 / dioxane; H2O / 2 h / 20 °C 5: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 6: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

1: 82 percent / aq. NH4OH; iodine; aq. KI / dioxane / 0.83 h / ice cooling 2: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 80 °C 3: 92 percent / OsO4; 2-methyl-2-propanol; NaIO4 / dioxane; H2O / 2 h / 20 °C 4: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 5: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

1: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 80 °C 2: 92 percent / OsO4; 2-methyl-2-propanol; NaIO4 / dioxane; H2O / 2 h / 20 °C 3: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 4: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

1: 92 percent / OsO4; 2-methyl-2-propanol; NaIO4 / dioxane; H2O / 2 h / 20 °C 2: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 3: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

1: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 2: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

1: 80 percent / NaIO4 / tetrahydrofuran; H2O / 72 h / 20 °C 2: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 3: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

potassium carbonate; acetone