1: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.75 h / -80 °C 2: 71 percent / CrO3, pyridine / CH2Cl2 / 0.33 h / 10 °C 3: 87 percent / NEt3 / CH2Cl2 / 48 h / Ambient temperature 4: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 5: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 6: 86 percent / K2CO3 / 1 h / 23 °C 7: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 8: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme

1: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 2: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme

1: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 2: 86 percent / K2CO3 / 1 h / 23 °C 3: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 4: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme

1: 86 percent / K2CO3 / 1 h / 23 °C 2: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 3: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme

1: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 2: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 3: 86 percent / K2CO3 / 1 h / 23 °C 4: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 5: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme

1: With Physcomitrella patens lipoxygenase PpLOX2; oxygen pH=7.0; 0.5 h; aq. phosphate bufferEnzymatic reaction; 2: With sodium tetrahydroborate in methanol 0.5 h; enantiospecific reaction;

1: n-Bu4NF 2: 79 percent / LiOH View Scheme

1: 1.) (Sia)2BH, AcOH; 2.) H2O2, NaOH / 1.) THF 2: n-Bu4NF 3: 79 percent / LiOH View Scheme

1: With Physcomitrella patens lipoxygenase PpLOX7; oxygen pH=7.0; 0.5 h; aq. phosphate bufferEnzymatic reaction; 2: With sodium tetrahydroborate in methanol 0.5 h; enantiospecific reaction;

microsomes of mutton vesicular glands; oxygen in octane; water T=25°C; 1 h; potassium phosphate buffer (pH 7.4) presence, n-octane absence; Product distribution;