1: 74 percent / KOH / ethanol / 15 h / Heating 2: 68 percent / Na2CO3 / methanol / 1 h / 80 °C View Scheme

1: 50 mg / lithium aluminum hydride, aluminum chloride / tetrahydrofuran / 1 h / Heating 2: 27 percent / acetic acid, lead tetraacetate / 16 h / Ambient temperature View Scheme

1: H2, acetic acid / 5percent Pd/C / 760 Torr / Ambient temperature 2: O2 / 5percent Pd/C / 18 h / Ambient temperature View Scheme

lead(IV) acetate; acetic acid 16 h; Ambient temperature;

1.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C 1.2: 3 h / 20 °C 2.1: sodium tetrahydroborate / methanol / 13 h / 20 °C / |Irradiation View Scheme

1.1: sodium amide / tetrahydrofuran / |Reflux; |Inert atmosphere; |Cooling with ice 2.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C 2.2: 3 h / 20 °C 3.1: sodium tetrahydroborate / methanol / 13 h / 20 °C / |Irradiation View Scheme

1.1: trifluoromethylsulfonic anhydride; pyridine / acetonitrile / 2 h / 20 °C / |Cooling with ice; |Inert atmosphere 1.2: 20 °C / |Inert atmosphere 2.1: sodium amide / tetrahydrofuran / |Reflux; |Inert atmosphere; |Cooling with ice 3.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C 3.2: 3 h / 20 °C 4.1: sodium tetrahydroborate / methanol / 13 h / 20 °C / |Irradiation View Scheme

(i) H2, Raney-Ni, EtOH, (ii) NaNO2, aq. H2SO4, MeOH, (iii) (heating); Multistep reaction;