in benzene T=80°C; Wittig reaction; 3 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;

1.1: OsO4 1.2: 80 percent / NaIO4 2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 5.1: 80 percent / PCC 6.1: LDA View Scheme

1.1: OsO4 1.2: 80 percent / NaIO4 2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 5.1: 80 percent / PCC 6.1: LDA 7.1: 88 percent / CSA / methanol 8.1: PCC 8.2: 90 percent / NaClO2 View Scheme

1.1: OsO4 1.2: 80 percent / NaIO4 2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 5.1: 80 percent / PCC 6.1: LDA View Scheme

1.1: imidazole / dimethylformamide 2.1: NMO; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran / 3 h / 0 °C 3.1: 5.56 g / Pb(OAc)4 / ethyl acetate / 2 h / 0 °C 4.1: 68 percent / PPh3 / CH2Cl2 / 0.25 h / -60 °C 5.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 5.2: 65 percent / tetrahydrofuran / 6 h / -78 - 20 °C 6.1: 74 percent / 4 Angstroem molecular sieves; TBAF*3H2O / tetrahydrofuran / 3 h 7.1: 81 percent / DCC; DMAP / CH2Cl2 / 14 h / 20 °C 8.1: 80 percent / CH2Cl2 / [Mo{(t-Bu)(3,5-dimethylphenyl)N}3] / toluene / 8 h / 80 °C 9.1: 99 percent / quinoline; H2 / Lindlar catalyst / hexane; CH2Cl2 / 8 h / 20 °C 10.1: 79 percent / aq. HF / acetonitrile; diethyl ether / 8 h / 20 °C View Scheme

1: in diethyl ether T=-78°C; 3 h; Inert atmosphere; 2: With dihydrogen peroxide; sodium acetate in water T=0 - 20°C; 0.333333 h;

titanium(IV) isopropylate; (S)-(minus;)-1,1'-bi-2-naphthol in dichloromethane T=-78 - -20°C; 120.5 h; Molecular sieveInert atmosphere; optical yield given as percent eeenantioselective reaction;

in diethyl ether; pentane T=-100°C; 1 h;

(S)-BINOL-Ti(OiPr)4 Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

in diethyl ether; pentane T=-100°C; 0.5 h;