1: 1.) ethylmagnesium bromide / 1.) THF, r.t., 1.5 h; 2.) THF, r.t., 1 h 2: 81 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 55 °C 3: 60 percent / LiAlH4, titanium trichloride, triethylamine / tetrahydrofuran; diethyl ether / 0.5 h / 50 °C View Scheme

1: 1.) ethylmagnesium bromide / 1.) THF, r.t, 1.5 h; 2.) THF, r.t., 1 h 2: 70 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 55 °C 3: 60 percent / titanium trichloride, LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature 4: 7 percent Spectr. / O-mesitylenesulfonyl hydroxylamine / CH2Cl2 / 0.17 h / -95 °C View Scheme

1: 90 percent / EtMgBr 2: 1.) DIBAL 3: 85 percent / Lindlar 4: 85 percent / LiAlH4,TiCl3 / tetrahydrofuran / 0.75 h / Ambient temperature 5: 80 percent / Bu4N(1+)F(1-) View Scheme

1: 1.) ethylmagnesium bromide / 1.) THF, r.t., 1.5 h; 2.) THF, r.t., 1 h 2: 81 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 55 °C 3: 60 percent / LiAlH4, titanium trichloride, triethylamine / tetrahydrofuran; diethyl ether / 0.5 h / 50 °C View Scheme

1: 64 percent / 1.) n-BuLi / 1.) ether, -10 deg C, 20 min, 2.) -10 deg C -> RT, 1,5 h; RT, 1.5 h 2: 375 mg / diethyl ether; pentane / -78 deg C, 5 h, then -> RT, 0.5 h 3: 2.) tetra-n-butylammonium fluoride / 1.) hexane, reflux, 2 h, 2.) THF, 1 h 4: 80 percent / MnO2 / light petroleum / 1 h / 4 °C View Scheme

1: 1.) ethylmagnesium bromide / 1.) THF, r.t., 1.5 h; 2.) THF, r.t., 1 h 2: 81 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 55 °C 3: 60 percent / LiAlH4, titanium trichloride, triethylamine / tetrahydrofuran; diethyl ether / 0.5 h / 50 °C 4: 1.) collidine, silver nitrate; 2.) silica gel / 1.) acetonitrile; 2.) column chromatography with hexane-ether View Scheme

1: 1.) ethylmagnesium bromide / 1.) THF, r.t, 1.5 h; 2.) THF, r.t., 1 h 2: 70 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 55 °C 3: 60 percent / titanium trichloride, LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature 4: 80 percent / O-mesitylenesulfonyl hydroxylamine / CH2Cl2 / 0.17 h / -95 °C View Scheme

1: 1.) ethylmagnesium bromide / 1.) THF, r.t., 1.5 h; 2.) THF, r.t., 1 h 2: 81 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 55 °C 3: 60 percent / LiAlH4, titanium trichloride, triethylamine / tetrahydrofuran; diethyl ether / 0.5 h / 50 °C 4: 1.) collidine, silver nitrate; 2.) silica gel / 1.) acetonitrile; 2.) column chromatography with hexane-ether View Scheme

Ozonolyse;