1: piperidine acetate / xylene / 4 h / Heating 2: TsOH / 24 h / Ambient temperature 3: 93 percent / DIBAH / diethyl ether; toluene / 1.5 h / -20 °C 4: 97 percent / pyridine / 18 h / -5 - 0 °C 5: 82 percent / LiAlH4 / diethyl ether / 1.5 h 6: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h 7: 92 percent / pyridine / 24 h / Ambient temperature View Scheme

1: piperidine acetate / xylene / 4 h / Heating 2: TsOH / 24 h / Ambient temperature 3: 93 percent / DIBAH / diethyl ether; toluene / 1.5 h / -20 °C 4: 97 percent / pyridine / 18 h / -5 - 0 °C 5: 82 percent / LiAlH4 / diethyl ether / 1.5 h 6: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h 7: 76 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

1: piperidine acetate / xylene / 4 h / Heating 2: TsOH / 24 h / Ambient temperature 3: 93 percent / DIBAH / diethyl ether; toluene / 1.5 h / -20 °C 4: 97 percent / pyridine / 18 h / -5 - 0 °C 5: 82 percent / LiAlH4 / diethyl ether / 1.5 h 6: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h View Scheme

diisobutylaluminium hydride in hexane; toluene 1.) 0 deg C, 3 h, 2.) 10 deg C, 1 h;

1: 11-bromo-undec-1-ene With magnesium; ethylene dibromide in tetrahydrofuran 2 h; Inert atmosphere; 2: N,N-dimethyl-formamide in tetrahydrofuran T=0 - 20°C; 0.333333 h; Inert atmosphere;

1: dimethylsulfoxide / 1 h / 100 °C 2: 86 percent / DIBAL-H / toluene; hexane / 1.) 0 deg C, 3 h, 2.) 10 deg C, 1 h View Scheme

tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide in dichloromethane T=20°C; 1 h; Molecular sieveInert atmosphere;

1: pyridine 2: dimethylsulfoxide / 1 h / 100 °C 3: 86 percent / DIBAL-H / toluene; hexane / 1.) 0 deg C, 3 h, 2.) 10 deg C, 1 h View Scheme

1: 90 percent / NaAlH2(OCH2CH2OCH3)2 / benzene / 1 h / Heating 2: 95 percent / 1.) Et3N; 2.) lactic acid / CH2Cl2 / 0 °C 3: 95 percent / dimethylsulfoxide / 24 h 4: 1.) diisobutylaluminum hydride; 2.) HCl / 1.) benzene, hexane, 1 h; 2.) 0 deg C, MeOH, ether View Scheme

in tetrahydrofuran 2 h; Ambient temperature;