1.1: 86 percent / NaH / tetrahydrofuran / 12 h / 20 °C 2.1: ozone / CH2Cl2 / 2 h 2.2: 81 percent / triphenylphosphine / CH2Cl2 / 40 h / 0 °C View Scheme

1.1: O3; TPP / CH2Cl2 / -78 °C 1.2: 78 percent / CH2Cl2 / 20 °C 2.1: 84 percent / DIBAL-H / CH2Cl2 / 1 h / 0 - 20 °C 3.1: CH2Cl2 4.1: K2CO3 / methanol / 20 °C 5.1: 98 percent / DIPEA; DMAP / CH2Cl2 / 0 - 20 °C 6.1: 90 percent / Na; NH3 / tetrahydrofuran / 0.75 h 7.1: 95 percent / H2 / PtO2 / ethyl acetate / 1 h / 20 °C 8.1: 94 percent / NaH; TBAI / tetrahydrofuran / 0 - 20 °C 9.1: 92 percent / BF3*OEt2; ethane dithiol / CH2Cl2 / 1 h / 0 - 20 °C 10.1: TEMPO; BAIB / CH2Cl2 / 20 °C 11.1: NaClO2; NaH2PO4 12.1: 78 percent / PhSO2Cl; pyridine / 12 h / 0 °C 13.1: 91 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h View Scheme

1.1: O3; TPP / CH2Cl2 / -78 °C 1.2: 78 percent / CH2Cl2 / 20 °C 2.1: 84 percent / DIBAL-H / CH2Cl2 / 1 h / 0 - 20 °C 3.1: CH2Cl2 4.1: K2CO3 / methanol / 20 °C 5.1: 98 percent / DIPEA; DMAP / CH2Cl2 / 0 - 20 °C 6.1: 90 percent / Na; NH3 / tetrahydrofuran / 0.75 h 7.1: 95 percent / H2 / PtO2 / ethyl acetate / 1 h / 20 °C 8.1: 94 percent / NaH; TBAI / tetrahydrofuran / 0 - 20 °C 9.1: 92 percent / BF3*OEt2; ethane dithiol / CH2Cl2 / 1 h / 0 - 20 °C 10.1: TEMPO; BAIB / CH2Cl2 / 20 °C 11.1: NaClO2; NaH2PO4 12.1: 78 percent / PhSO2Cl; pyridine / 12 h / 0 °C 13.1: 91 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h 14.1: 90 percent / DIAD; TPP / tetrahydrofuran / 3 h / 0 - 20 °C View Scheme

1: OsO4; NMO 2: NaIO4 3: NaClO2; KH2PO4 View Scheme

1.1: O3; TPP / CH2Cl2 / -78 °C 1.2: 78 percent / CH2Cl2 / 20 °C 2.1: 84 percent / DIBAL-H / CH2Cl2 / 1 h / 0 - 20 °C 3.1: CH2Cl2 4.1: K2CO3 / methanol / 20 °C 5.1: 98 percent / DIPEA; DMAP / CH2Cl2 / 0 - 20 °C 6.1: 90 percent / Na; NH3 / tetrahydrofuran / 0.75 h 7.1: 95 percent / H2 / PtO2 / ethyl acetate / 1 h / 20 °C 8.1: 94 percent / NaH; TBAI / tetrahydrofuran / 0 - 20 °C 9.1: 92 percent / BF3*OEt2; ethane dithiol / CH2Cl2 / 1 h / 0 - 20 °C 10.1: TEMPO; BAIB / CH2Cl2 / 20 °C 11.1: NaClO2; NaH2PO4 12.1: 78 percent / PhSO2Cl; pyridine / 12 h / 0 °C 13.1: 91 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h View Scheme