1: 53 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 20 °C 2: 78 percent / Pr4NRuO4; NMO; MS4A / acetonitrile 3: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 4: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 5: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C 6: 86 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

1: 1.) 48 percent HBr, concd. H2SO4; 2.) KMnO4 / 1.) 3 h, reflux; 2.) 20percent H2SO4, 15-20 deg C 3: 75 percent / NaBH4 / ethanol / 13 h / Ambient temperature 4: 80 percent / aq. H2O2 / tetrahydrofuran / 24 h 6: aq. KOH / 0.5 h / Heating View Scheme

1: 1.) NaH; 2.) (COCl)2, DMSO / 1.) THF, 60 deg C; 2.) CH2Cl2, r.t. 2: 83 percent / tetrahydrofuran / 0 °C 3: 89 percent / (COCl)2, DMSO / CH2Cl2 / Ambient temperature 4: 90 percent / FeCl3 / CH2Cl2 / Ambient temperature 5: 92 percent / p-TsOH 6: (COCl)2, DMSO / CH2Cl2 / Ambient temperature 7: KN(SiMe3)2 / tetrahydrofuran / 0 °C 8: 1.) PhSSPh; 2.) BF3*Et2O / 1.) irrad.,r.t., hexane; 2.) CH2Cl2, r.t. 9: 1N NaOH / methanol 10: SOCl2 / benzene / Heating 11: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 12: 97 percent / NaBH4 / methanol / 0 °C 13: NCS, AgNO3 14: 10percent MeOH, CF3COOH / 60 °C 15: 68 percent / 2N NaOH / methanol / Ambient temperature 16: H2 / 10percent Pd/C / methanol View Scheme

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3 h / 20 °C 3.1: R-(+)-proline / chloroform / 2 h / 0 °C 3.2: 2 h / 0 °C 4.1: acetic acid; zinc / ethanol / 12 h / 20 °C 5.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0 - 20 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / |Reflux; |Inert atmosphere 7.1: 1H-imidazole / dichloromethane / 0.17 h / 0 °C 7.2: 6 h / 0 - 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 - 20 °C 9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3 h / 20 °C 10.1: (S)-(minus;)-1,1'-bi-2-naphthol; titanium (IV) isopropoxide / dichloromethane / 0.5 h / 20 °C / |Inert atmosphere; |Molecular sieve 10.2: 24 h / -78 - -20 °C / |Inert atmosphere; |Molecular sieve 11.1: 4-(N,N-dimethlyamino)pyridine / 1 h / 0 - 20 °C / |Inert atmosphere 12.1: Grubb's 2nd generation catalyst / dichloromethane 13.1: 0.5 h / 0 - 20 °C View Scheme

1: 1.) 48 percent HBr, concd. H2SO4; 2.) KMnO4 / 1.) 3 h, reflux; 2.) 20percent H2SO4, 15-20 deg C View Scheme

View Scheme

Dowex 50W x 2 (50-100 mesh) in toluene T=30°C; 4.5 h;

copper(II) sulfate in acetonitrile T=20°C; 12 h;

Dowex 50W x 2 in toluene T=30°C; Etherification; hydration; 4.5 h;

di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; triphenylphosphine; potassium hydroxide in toluene T=100°C; 2 h; Inert atmosphere;