n-butyllithium 1.) Et2O-hexane, 10 min, 2.) 5 h;

T=68°C; 72 h;

1: 1) p-TsOH*H2O / 1) benzene, reflux, 1 h; 2) ether 2: 9.5 g / aq. 5 percent HCl, acetone / 1 h / Heating 3: 13.5 g / p-TsOH*H2O / benzene / 1 h / Heating 4: 1) LiAlH4; 2) EtOAc, water, aq. 4 N NaOH / 1) THF, 1 h; 2) RT, 1 h 5: 99 percent / tri-n-butylphosphine / pyridine / 23 h / 60 °C 6: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h 7: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating 8: p-TsOH*H2O / benzene / 0.5 h / Heating View Scheme

1: 1.) NaOMe / 1.) THF, 20 min, 2.) THF, reflux, 6 h 2: KOH / bis-(2-hydroxy-ethyl) ether / 12 h / 200 °C View Scheme

1: 1.) NaOMe / 1.) THF, 20 min, 2.) THF, reflux, 6 h 2: KOH / bis-(2-hydroxy-ethyl) ether / 12 h / 200 °C 3: POCl3 / 4 h / Ambient temperature View Scheme

1: 1.) NaOMe / 1.) THF, 20 min, 2.) THF, reflux, 6 h 2: KOH / bis-(2-hydroxy-ethyl) ether / 12 h / 200 °C 3: POCl3 / 4 h / Ambient temperature 4: Et3N / diethyl ether / 3 h / Ambient temperature View Scheme

hydrogenchloride; water 16 h; Heating;

1: 1) p-TsOH*H2O / 1) benzene, reflux, 1 h; 2) ether 2: 9.5 g / aq. 5 percent HCl, acetone / 1 h / Heating View Scheme

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