ammonia; lithium in tetrahydrofuran 2 h; cooling;

1.1: 60 percent / PTSA / CH2Cl2 / 0.5 h 2.1: 90 percent / (COCl)2; DMSO; Et3N / dimethylsulfoxide; CH2Cl2 / -78 - 25 °C 3.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 1 h / 0 °C 3.2: tetrahydrofuran; hexane / 0 °C 4.1: PTSA / methanol / 1 h / 20 °C 5.1: 75 percent / Jones reagent / acetone / 0 - 20 °C 6.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: NaH / tetrahydrofuran / 1 h / 0 °C 1.2: 80 percent / tetrabutylammonium iodide / tetrahydrofuran / 2 h / 20 °C 2.1: 82 percent / CSA / cyclohexane; CH2Cl2 / 24 h / 20 °C 3.1: 80 percent / DDQ / CH2Cl2; H2O / 1 h / 20 °C 4.1: 65 percent / DMP / CH2Cl2 / 0 - 20 °C 5.1: NaHMDS; HMPA / tetrahydrofuran / 1 h / -30 °C 5.2: 40 percent / tetrahydrofuran / -30 - 20 °C 6.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: O2; Lipoxygenase type-1; aq. sodium borate buffer / 1 h / 0 °C / pH 9.0 1.2: 40 percent / HRP / aq. phosphate buffer / 1 h / 20 °C / pH 6.5 2.1: 90 percent / KOH / methanol / 12 h / 20 °C 3.1: NaH / tetrahydrofuran / 1 h / 0 °C 3.2: 80 percent / tetrabutylammonium iodide / tetrahydrofuran / 2 h / 20 °C 4.1: 82 percent / CSA / cyclohexane; CH2Cl2 / 24 h / 20 °C 5.1: 80 percent / DDQ / CH2Cl2; H2O / 1 h / 20 °C 6.1: 65 percent / DMP / CH2Cl2 / 0 - 20 °C 7.1: NaHMDS; HMPA / tetrahydrofuran / 1 h / -30 °C 7.2: 40 percent / tetrahydrofuran / -30 - 20 °C 8.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: 90 percent / KOH / methanol / 12 h / 20 °C 2.1: NaH / tetrahydrofuran / 1 h / 0 °C 2.2: 80 percent / tetrabutylammonium iodide / tetrahydrofuran / 2 h / 20 °C 3.1: 82 percent / CSA / cyclohexane; CH2Cl2 / 24 h / 20 °C 4.1: 80 percent / DDQ / CH2Cl2; H2O / 1 h / 20 °C 5.1: 65 percent / DMP / CH2Cl2 / 0 - 20 °C 6.1: NaHMDS; HMPA / tetrahydrofuran / 1 h / -30 °C 6.2: 40 percent / tetrahydrofuran / -30 - 20 °C 7.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: 65 percent / DMP / CH2Cl2 / 0 - 20 °C 2.1: NaHMDS; HMPA / tetrahydrofuran / 1 h / -30 °C 2.2: 40 percent / tetrahydrofuran / -30 - 20 °C 3.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: 82 percent / CSA / cyclohexane; CH2Cl2 / 24 h / 20 °C 2.1: 80 percent / DDQ / CH2Cl2; H2O / 1 h / 20 °C 3.1: 65 percent / DMP / CH2Cl2 / 0 - 20 °C 4.1: NaHMDS; HMPA / tetrahydrofuran / 1 h / -30 °C 4.2: 40 percent / tetrahydrofuran / -30 - 20 °C 5.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: 80 percent / DDQ / CH2Cl2; H2O / 1 h / 20 °C 2.1: 65 percent / DMP / CH2Cl2 / 0 - 20 °C 3.1: NaHMDS; HMPA / tetrahydrofuran / 1 h / -30 °C 3.2: 40 percent / tetrahydrofuran / -30 - 20 °C 4.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: 90 percent / (COCl)2; DMSO; Et3N / dimethylsulfoxide; CH2Cl2 / -78 - 25 °C 2.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 1 h / 0 °C 2.2: tetrahydrofuran; hexane / 0 °C 3.1: PTSA / methanol / 1 h / 20 °C 4.1: 75 percent / Jones reagent / acetone / 0 - 20 °C 5.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 1 h / 0 °C 1.2: tetrahydrofuran; hexane / 0 °C 2.1: PTSA / methanol / 1 h / 20 °C 3.1: 75 percent / Jones reagent / acetone / 0 - 20 °C 4.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme