sulfuric acid T=5 - 7°C;

Oxonereg;; sodium hydrogencarbonate; potassium carbonate in acetone T=18°C; Nef reaction; 29 h;

sodium azide; sodium methylate in methanol T=8 - 10°C; Electrolysis;

1.1: 95 percent / aq. NaHCO3; K2CO3; Oxone / acetone / 29 h / 18 °C 2.1: NaHMDS / tetrahydrofuran / 1.5 h / 18 °C 2.2: 30 percent / tetrahydrofuran / 15 h / 18 °C 3.1: 57 percent / LiAlH4 / diethyl ether / 1.5 h 4.1: 70 percent / NaH; NaI / dimethylformamide / 18 h / 18 °C 5.1: Rh2(OAc)4 / CH2Cl2 / 0.5 h / 18 °C 6.1: 210 mg / H2 / 5percent Pd/C / CH2Cl2; ethyl acetate; ethanol / 22 h / 18 °C / 760.05 Torr View Scheme

(i) H2, Raney-Ni, (ii) aq. HCl; Multistep reaction;

Multi-step reaction with 5 steps 1.1: 95 percent / aq. NaHCO3; K2CO3; Oxone / acetone / 29 h / 18 °C2.1: NaHMDS / tetrahydrofuran / 1.5 h / 18 °C2.2: 30 percent / tetrahydrofuran / 15 h / 18 °C3.1: 57 percent / LiAlH4 / diethyl ether / 1.5 h4.1: 70 percent / NaH; NaI / dimethylformamide / 18 h / 18 °C5.1: Rh2(OAc)4 / CH2Cl2 / 0.5 h / 18 °C