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: 99 percent / TBAF, 4 Angstroem molecular sieves / tetrahydrofuran / -78 °C 2: 80 percent / DCC, 4-DMAP / CH2Cl2 / 12 h / Ambient temperature 3: 94 percent / <RuCHPh>Cl2*(PCy3)2 / CH2Cl2 / 12 h / Ambient temperature 4: 65 percent / HF / acetonitrile; diethyl ether / 12 h / Ambient temperature 5: 48 percent / dimethyl dioxirane / CH2Cl2 / 2 h / -35 °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

1.1: 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 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: 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: NMO; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran / 3 h / 0 °C 2.1: 5.56 g / Pb(OAc)4 / ethyl acetate / 2 h / 0 °C 3.1: 68 percent / PPh3 / CH2Cl2 / 0.25 h / -60 °C 4.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 4.2: 65 percent / tetrahydrofuran / 6 h / -78 - 20 °C 5.1: 74 percent / 4 Angstroem molecular sieves; TBAF*3H2O / tetrahydrofuran / 3 h 6.1: 81 percent / DCC; DMAP / CH2Cl2 / 14 h / 20 °C 7.1: 80 percent / CH2Cl2 / [Mo{(t-Bu)(3,5-dimethylphenyl)N}3] / toluene / 8 h / 80 °C 8.1: 99 percent / quinoline; H2 / Lindlar catalyst / hexane; CH2Cl2 / 8 h / 20 °C 9.1: 79 percent / aq. HF / acetonitrile; diethyl ether / 8 h / 20 °C View Scheme

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