1: 97 percent / Zn / tetrahydrofuran / 1 h / 20 °C 2: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 3: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 4: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 5: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 6: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 7: H2 View Scheme

1.1: DMF; oxalyl chloride / acetonitrile; tetrahydrofuran; pyridine / 1.5 h / -30 °C 1.2: 63 percent / CuI; tri-tert-butoxyaluminium hydride / acetonitrile; tetrahydrofuran; pyridine / 0.25 h / -78 °C 2.1: 97 percent / Zn / tetrahydrofuran / 1 h / 20 °C 3.1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 4.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 5.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 6.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 7.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 8.1: H2 View Scheme

1: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C 2: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme

bioconversion, by cell suspension of Nicotiana plumbaginifolia;

1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 2: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 3: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 4: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 6: H2 View Scheme

1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 2: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 3: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 4: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 5: H2 View Scheme

1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 2: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 3: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 4: H2 View Scheme

1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 2: H2 View Scheme

1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 2: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 3: H2 View Scheme

1.1: 82 percent / (COCl)2; NEt3 / dimethylsulfoxide 2.1: molecular sieves 4 Angstroem / CH2Cl2 / 16 h / 20 °C 2.2: 45 percent / NaCNBH3 / methanol; acetic acid / 16 h / 0 - 20 °C 3.1: 95 percent / aq. HCl; methanol View Scheme