Streptomyces EUSA-2003B; cyclodextrin in N,N-dimethyl-formamide T=26 - 28°C; 120 h; Microbiological reactionstarch-nitrate liquid medium;

1: 86 percent / pyridiniumchlorochromate, NaAc*3H2O / CH2Cl2 / 0.42 h / Ambient temperature 2: 2.) CH3COOH, CF3COOH, H2O / 1.) CH2Cl2, room temp., 30 min, irradiation; 2.) THF, 15 degC, 24h 3: 95 percent / 1.5percent methanolic HCl / 16 h / Ambient temperature View Scheme

1: 69 percent / MnO2 / CH2Cl2 / 1 h / Ambient temperature 2: 1.) K-tert-C4H9 / 1.) -25 degC, 10 min, ether; 2.) -25 degC to room temp. in 30 min 3: O2, Bengalrosa B / CH2Cl2 / 0.17 h / 25 °C / Irradiation 4: triethylamine / CH2Cl2 / 0.08 h / Ambient temperature 5: 64 percent / 16 h / 40 °C 6: 86 percent / pyridiniumchlorochromate, NaAc*3H2O / CH2Cl2 / 0.42 h / Ambient temperature 7: 2.) CH3COOH, CF3COOH, H2O / 1.) CH2Cl2, room temp., 30 min, irradiation; 2.) THF, 15 degC, 24h 8: 95 percent / 1.5percent methanolic HCl / 16 h / Ambient temperature View Scheme

1: 1.) K-tert-C4H9 / 1.) -25 degC, 10 min, ether; 2.) -25 degC to room temp. in 30 min 2: O2, Bengalrosa B / CH2Cl2 / 0.17 h / 25 °C / Irradiation 3: triethylamine / CH2Cl2 / 0.08 h / Ambient temperature 4: 64 percent / 16 h / 40 °C 5: 86 percent / pyridiniumchlorochromate, NaAc*3H2O / CH2Cl2 / 0.42 h / Ambient temperature 6: 2.) CH3COOH, CF3COOH, H2O / 1.) CH2Cl2, room temp., 30 min, irradiation; 2.) THF, 15 degC, 24h 7: 95 percent / 1.5percent methanolic HCl / 16 h / Ambient temperature View Scheme

1: O2, Bengalrosa B / CH2Cl2 / 0.17 h / 25 °C / Irradiation 2: triethylamine / CH2Cl2 / 0.08 h / Ambient temperature 3: 64 percent / 16 h / 40 °C 4: 86 percent / pyridiniumchlorochromate, NaAc*3H2O / CH2Cl2 / 0.42 h / Ambient temperature 5: 2.) CH3COOH, CF3COOH, H2O / 1.) CH2Cl2, room temp., 30 min, irradiation; 2.) THF, 15 degC, 24h 6: 95 percent / 1.5percent methanolic HCl / 16 h / Ambient temperature View Scheme

1: 64 percent / 16 h / 40 °C 2: 86 percent / pyridiniumchlorochromate, NaAc*3H2O / CH2Cl2 / 0.42 h / Ambient temperature 3: 2.) CH3COOH, CF3COOH, H2O / 1.) CH2Cl2, room temp., 30 min, irradiation; 2.) THF, 15 degC, 24h 4: 95 percent / 1.5percent methanolic HCl / 16 h / Ambient temperature View Scheme

1: triethylamine / CH2Cl2 / 0.08 h / Ambient temperature 2: 64 percent / 16 h / 40 °C 3: 86 percent / pyridiniumchlorochromate, NaAc*3H2O / CH2Cl2 / 0.42 h / Ambient temperature 4: 2.) CH3COOH, CF3COOH, H2O / 1.) CH2Cl2, room temp., 30 min, irradiation; 2.) THF, 15 degC, 24h 5: 95 percent / 1.5percent methanolic HCl / 16 h / Ambient temperature View Scheme

1: 25 percent / LiAlH4, tert-BuOH / tetrahydrofuran / 3 h / Ambient temperature 2: 95 percent / 1.5percent methanolic HCl / 16 h / Ambient temperature View Scheme

hydrogenchloride; methanol; water

hydrogenchloride; methanol; water