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 View Scheme

1.1: 96 percent / 4-DMAP; Et3N / CH2Cl2 / 2 h 2.1: N-methylmorpholine N-oxide; water / OsO4 / acetone; butan-1-ol / 2 h / 0 °C 3.1: NaIO4 / tetrahydrofuran; H2O / 1.25 h / 20 °C 4.1: 0.014 g / HMPA / tetrahydrofuran / 0.5 h / -78 - 20 °C 5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 5.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 6.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 7.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 8.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 9.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 10.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 11.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 12.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C 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 9.1: 73 percent / TBAF 10.1: 77 percent / TCBCl; DIEA; DMAP 11.1: 59 percent / HF*pyr 12.1: 65 percent / mCPBA View Scheme

1: EDC; DMAP / CH2Cl2 2: 59 percent / second-generation Grubbs catalyst / CH2Cl2 / 6 h / Heating 3: TFA / CH2Cl2 / 0 - 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;

4 A molecular sieve; tetrabutyl ammonium fluoride in tetrahydrofuran T=-78°C;

hydrogen; palladium on activated charcoal in tetrahydrofuran T=20°C; 1 h;

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

1: 83 percent / benzene / Heating 2: 60 percent / (S)-(-)-1,1'-bi-2-naphthol; Ti(O-i-Pr)4; 4 Angstroem sieves / CH2Cl2 / 70 h / -78 - -20 °C View Scheme