tert.-butyl lithium in tetrahydrofuran T=-78°C;

hydrogen; platinum(IV) oxide in ethanol

potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate in tetrahydrofuran 24 h; Ambient temperature;

sodium tetrahydroborate in methanol; acetonitrile Irradiation;

1: 97 percent / 5percent KOH / methanol; H2O 2: NEt3 / tetrahydrofuran / 0.75 h / -10 °C 3: 59 percent / tetrahydrofuran / Ambient temperature 4: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 5: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C 6: 90 percent / H2 / PtO2 / ethanol View Scheme

1: 67 percent / NaCl, H2O / dimethylsulfoxide / 8 h / Heating 2: 97 percent / 5percent KOH / methanol; H2O 3: NEt3 / tetrahydrofuran / 0.75 h / -10 °C 4: 59 percent / tetrahydrofuran / Ambient temperature 5: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 6: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C 7: 90 percent / H2 / PtO2 / ethanol View Scheme

1: NEt3 / tetrahydrofuran / 0.75 h / -10 °C 2: 59 percent / tetrahydrofuran / Ambient temperature 3: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 4: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C 5: 90 percent / H2 / PtO2 / ethanol View Scheme

1: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C 2: 90 percent / H2 / PtO2 / ethanol View Scheme

1: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 2: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C 3: 90 percent / H2 / PtO2 / ethanol View Scheme

hydrogenchloride; tetracarbonylbis(μ-chloro)dirhodium(I) in tetrahydrofuran; diethyl ether T=100°C; P=51754.1 Torr; 40 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;