1: (3AS-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]-indol-5-ol With sodium hydride in tetrahydrofuran T=20°C; 0.166667 h; 2: phenyl isocyanate in tetrahydrofuran 4.5 h;

1.1: MgSO4 / tetrahydrofuran 1.2: 90 percent / LiAlH4 / tetrahydrofuran 2.1: BBr3 / CH2Cl2 / 3 h / 20 °C 3.1: NaH / tetrahydrofuran / 0.17 h / 20 °C 3.2: 3.22 g / tetrahydrofuran / 4.5 h View Scheme

1.1: BBr3 / CH2Cl2 / 3 h / 20 °C 2.1: NaH / tetrahydrofuran / 0.17 h / 20 °C 2.2: 3.22 g / tetrahydrofuran / 4.5 h View Scheme

1.1: 14.7 g / aq. NaIO4 / tetrahydrofuran / 22 h / 20 °C 2.1: MgSO4 / tetrahydrofuran 2.2: 90 percent / LiAlH4 / tetrahydrofuran 3.1: BBr3 / CH2Cl2 / 3 h / 20 °C 4.1: NaH / tetrahydrofuran / 0.17 h / 20 °C 4.2: 3.22 g / tetrahydrofuran / 4.5 h View Scheme

1.1: 90 percent / aq. p-toluenesulfonic acid / methanol / 79 °C 2.1: 14.7 g / aq. NaIO4 / tetrahydrofuran / 22 h / 20 °C 3.1: MgSO4 / tetrahydrofuran 3.2: 90 percent / LiAlH4 / tetrahydrofuran 4.1: BBr3 / CH2Cl2 / 3 h / 20 °C 5.1: NaH / tetrahydrofuran / 0.17 h / 20 °C 5.2: 3.22 g / tetrahydrofuran / 4.5 h View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C / Inert atmosphere 3.1: acetic acid / 0.25 h / 23 °C / Inert atmosphere 3.2: 0.25 h / 100 °C / Inert atmosphere 4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 80 °C / Inert atmosphere 5.1: boron tribromide / dichloromethane / 1.5 h / 23 °C / Inert atmosphere 6.1: sodium hydride / tetrahydrofuran / 14 h / 23 °C / Inert atmosphere 7.1: CHIRALPAK OJ-H (2 cm x 25 cm) / methanol; carbon dioxide; diethylamine / resolution of racemate; Supercritical conditions View Scheme

1: sodium hydride / tetrahydrofuran / 14 h / 23 °C / Inert atmosphere 2: CHIRALPAK OJ-H (2 cm x 25 cm) / methanol; carbon dioxide; diethylamine / resolution of racemate; Supercritical conditions View Scheme

1: boron tribromide / dichloromethane / 1.5 h / 23 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 14 h / 23 °C / Inert atmosphere 3: CHIRALPAK OJ-H (2 cm x 25 cm) / methanol; carbon dioxide; diethylamine / resolution of racemate; Supercritical conditions View Scheme