sodium tetrahydroborate 1.) ether, RT, 1 h, 2.) EtOH, 1 h; Multistep reaction. Title compound not separated from byproducts;

sodium tetrahydroborate 1.) ether, RT, 1 h, 2.) EtOH, 1 h; Multistep reaction. Title compound not separated from byproducts;

1: 2.) 10percent citric acid / 1.) a.) ether, reflux, 1 h, b.) RT, overnight, 2.) 2 h 2: 2 M H2SO4 / CHCl3 / Ambient temperature View Scheme

1: 2.) 10percent citric acid / 1.) a.) ether, reflux, 1 h, b.) RT, overnight, 2.) 2 h 2: 2 M H2SO4 / CHCl3 / Ambient temperature View Scheme

Yield given. Multistep reaction;

trimethylsilyl trifluoromethanesulfonate; triethylamine in dichloromethane T=20°C; 15 h; Yield given. Yields of byproduct given;

1: n-BuLi, diisopropylamine / hexane; tetrahydrofuran / 0.75 h / -50 °C 2: 20percent aq. H2SO4 / tetrahydrofuran; methanol / Ambient temperature 3: 64 percent / pyridine, thionyl chloride / CHCl3 / 6 h / 0 °C 4: DIBAL / tetrahydrofuran; toluene / 2 h / -30 °C 5: 10percent aq. H2SO4 / tetrahydrofuran; toluene / 0.5 h / -30 °C View Scheme

1: 1.) LDA; 2.) H2SO4; 3.) NaOH / 1.) -78 deg C -> 20 deg c, 1 h; 2.) MeOH; 3.) H2O 2: 89 percent / Et3N / Cl2Pd(PPh3)2 / acetonitrile; tetrahydrofuran / 18 h / 100 °C / 31028.9 Torr View Scheme