1.1: 87 percent / Et3N / CH2Cl2 / 72 h 2.1: 75 percent / AcOH; Water / tetrahydrofuran / 36 h / 45 °C 3.1: 100 percent / Et3N / CH2Cl2 / 20 °C 4.1: 82 percent / dimethylsulfoxide / 0.5 h 5.1: 93 percent / TBAF / tetrahydrofuran 6.1: Cp2ZrCl2 / hexane; 1,2-dichloro-ethane / 40 °C 6.2: 86 percent / I2 / tetrahydrofuran; hexane; 1,2-dichloro-ethane / 0.5 h / -30 - 0 °C 7.1: 62 percent / PdCl2(CH3CN)2 / dimethylformamide / 72 h / 20 °C 8.1: 80 percent / t-BuOOH; Ti(OiPr)4; L-(+)-DIPT / CH2Cl2; 2,2,4-trimethyl-pentane / 36 h / -24 °C 9.1: tetra-n-propylammonium perruthenate; NMO; 4 Angstroem molecular sieves / acetonitrile; CH2Cl2 / 0.67 h 10.1: KHMDS / toluene; tetrahydrofuran / 2 h 11.1: tetrahydrofuran / 0.75 h 11.2: CAN / acetonitrile / 5 h / 0 - 20 °C 12.1: 57 percent / MCPBA; K2CO3 / CH2Cl2 / 0.5 h 13.1: O3 / CH2Cl2 / 0.03 h / -78 °C 13.2: 18 percent / NaBH4/Al2O3 / benzene / 14 h / 20 °C 14.1: 40 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.08 h 15.1: 77 percent / TFA; anisole / CH2Cl2 / 0.42 h / -20 - -10 °C View Scheme

1.1: 100 percent / DIBAL-H / tetrahydrofuran; toluene / -78 °C 2.1: 87 percent / Et3N / CH2Cl2 / 72 h 3.1: 75 percent / AcOH; Water / tetrahydrofuran / 36 h / 45 °C 4.1: 100 percent / Et3N / CH2Cl2 / 20 °C 5.1: 82 percent / dimethylsulfoxide / 0.5 h 6.1: 93 percent / TBAF / tetrahydrofuran 7.1: Cp2ZrCl2 / hexane; 1,2-dichloro-ethane / 40 °C 7.2: 86 percent / I2 / tetrahydrofuran; hexane; 1,2-dichloro-ethane / 0.5 h / -30 - 0 °C 8.1: 62 percent / PdCl2(CH3CN)2 / dimethylformamide / 72 h / 20 °C 9.1: 80 percent / t-BuOOH; Ti(OiPr)4; L-(+)-DIPT / CH2Cl2; 2,2,4-trimethyl-pentane / 36 h / -24 °C 10.1: tetra-n-propylammonium perruthenate; NMO; 4 Angstroem molecular sieves / acetonitrile; CH2Cl2 / 0.67 h 11.1: KHMDS / toluene; tetrahydrofuran / 2 h 12.1: tetrahydrofuran / 0.75 h 12.2: CAN / acetonitrile / 5 h / 0 - 20 °C 13.1: 57 percent / MCPBA; K2CO3 / CH2Cl2 / 0.5 h 14.1: O3 / CH2Cl2 / 0.03 h / -78 °C 14.2: 18 percent / NaBH4/Al2O3 / benzene / 14 h / 20 °C 15.1: 40 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.08 h 16.1: 77 percent / TFA; anisole / CH2Cl2 / 0.42 h / -20 - -10 °C View Scheme

1.1: 100 percent / Et3N / CH2Cl2 / 20 °C 2.1: 82 percent / dimethylsulfoxide / 0.5 h 3.1: 93 percent / TBAF / tetrahydrofuran 4.1: Cp2ZrCl2 / hexane; 1,2-dichloro-ethane / 40 °C 4.2: 86 percent / I2 / tetrahydrofuran; hexane; 1,2-dichloro-ethane / 0.5 h / -30 - 0 °C 5.1: 62 percent / PdCl2(CH3CN)2 / dimethylformamide / 72 h / 20 °C 6.1: 80 percent / t-BuOOH; Ti(OiPr)4; L-(+)-DIPT / CH2Cl2; 2,2,4-trimethyl-pentane / 36 h / -24 °C 7.1: tetra-n-propylammonium perruthenate; NMO; 4 Angstroem molecular sieves / acetonitrile; CH2Cl2 / 0.67 h 8.1: KHMDS / toluene; tetrahydrofuran / 2 h 9.1: tetrahydrofuran / 0.75 h 9.2: CAN / acetonitrile / 5 h / 0 - 20 °C 10.1: 57 percent / MCPBA; K2CO3 / CH2Cl2 / 0.5 h 11.1: O3 / CH2Cl2 / 0.03 h / -78 °C 11.2: 18 percent / NaBH4/Al2O3 / benzene / 14 h / 20 °C 12.1: 40 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.08 h 13.1: 77 percent / TFA; anisole / CH2Cl2 / 0.42 h / -20 - -10 °C View Scheme

1.1: 93 percent / TBAF / tetrahydrofuran 2.1: Cp2ZrCl2 / hexane; 1,2-dichloro-ethane / 40 °C 2.2: 86 percent / I2 / tetrahydrofuran; hexane; 1,2-dichloro-ethane / 0.5 h / -30 - 0 °C 3.1: 62 percent / PdCl2(CH3CN)2 / dimethylformamide / 72 h / 20 °C 4.1: 80 percent / t-BuOOH; Ti(OiPr)4; L-(+)-DIPT / CH2Cl2; 2,2,4-trimethyl-pentane / 36 h / -24 °C 5.1: tetra-n-propylammonium perruthenate; NMO; 4 Angstroem molecular sieves / acetonitrile; CH2Cl2 / 0.67 h 6.1: KHMDS / toluene; tetrahydrofuran / 2 h 7.1: tetrahydrofuran / 0.75 h 7.2: CAN / acetonitrile / 5 h / 0 - 20 °C 8.1: 57 percent / MCPBA; K2CO3 / CH2Cl2 / 0.5 h 9.1: O3 / CH2Cl2 / 0.03 h / -78 °C 9.2: 18 percent / NaBH4/Al2O3 / benzene / 14 h / 20 °C 10.1: 40 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.08 h 11.1: 77 percent / TFA; anisole / CH2Cl2 / 0.42 h / -20 - -10 °C View Scheme

1.1: 75 percent / AcOH; Water / tetrahydrofuran / 36 h / 45 °C 2.1: 100 percent / Et3N / CH2Cl2 / 20 °C 3.1: 82 percent / dimethylsulfoxide / 0.5 h 4.1: 93 percent / TBAF / tetrahydrofuran 5.1: Cp2ZrCl2 / hexane; 1,2-dichloro-ethane / 40 °C 5.2: 86 percent / I2 / tetrahydrofuran; hexane; 1,2-dichloro-ethane / 0.5 h / -30 - 0 °C 6.1: 62 percent / PdCl2(CH3CN)2 / dimethylformamide / 72 h / 20 °C 7.1: 80 percent / t-BuOOH; Ti(OiPr)4; L-(+)-DIPT / CH2Cl2; 2,2,4-trimethyl-pentane / 36 h / -24 °C 8.1: tetra-n-propylammonium perruthenate; NMO; 4 Angstroem molecular sieves / acetonitrile; CH2Cl2 / 0.67 h 9.1: KHMDS / toluene; tetrahydrofuran / 2 h 10.1: tetrahydrofuran / 0.75 h 10.2: CAN / acetonitrile / 5 h / 0 - 20 °C 11.1: 57 percent / MCPBA; K2CO3 / CH2Cl2 / 0.5 h 12.1: O3 / CH2Cl2 / 0.03 h / -78 °C 12.2: 18 percent / NaBH4/Al2O3 / benzene / 14 h / 20 °C 13.1: 40 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.08 h 14.1: 77 percent / TFA; anisole / CH2Cl2 / 0.42 h / -20 - -10 °C View Scheme

1.1: 82 percent / dimethylsulfoxide / 0.5 h 2.1: 93 percent / TBAF / tetrahydrofuran 3.1: Cp2ZrCl2 / hexane; 1,2-dichloro-ethane / 40 °C 3.2: 86 percent / I2 / tetrahydrofuran; hexane; 1,2-dichloro-ethane / 0.5 h / -30 - 0 °C 4.1: 62 percent / PdCl2(CH3CN)2 / dimethylformamide / 72 h / 20 °C 5.1: 80 percent / t-BuOOH; Ti(OiPr)4; L-(+)-DIPT / CH2Cl2; 2,2,4-trimethyl-pentane / 36 h / -24 °C 6.1: tetra-n-propylammonium perruthenate; NMO; 4 Angstroem molecular sieves / acetonitrile; CH2Cl2 / 0.67 h 7.1: KHMDS / toluene; tetrahydrofuran / 2 h 8.1: tetrahydrofuran / 0.75 h 8.2: CAN / acetonitrile / 5 h / 0 - 20 °C 9.1: 57 percent / MCPBA; K2CO3 / CH2Cl2 / 0.5 h 10.1: O3 / CH2Cl2 / 0.03 h / -78 °C 10.2: 18 percent / NaBH4/Al2O3 / benzene / 14 h / 20 °C 11.1: 40 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.08 h 12.1: 77 percent / TFA; anisole / CH2Cl2 / 0.42 h / -20 - -10 °C View Scheme

1: 1.) 2,2,6,6-tetramethyl-1-oxopiperidinium chloride, 2.) NaClO2, NaH2PO4*H2O / 1.) CH2Cl2, -20 deg C, 10 min, then -15 deg C, 2 h, 2.) 2-methylbutene, H2O 2: 70 percent / benzenesulfonyl chloride, pyridine / 18.5 h / 0 - 10 °C 3: 78 percent / aq. HF / tetrahydrofuran / 8.5 h View Scheme

1: 70 percent / benzenesulfonyl chloride, pyridine / 18.5 h / 0 - 10 °C 2: 78 percent / aq. HF / tetrahydrofuran / 8.5 h View Scheme

3: 79 percent / N,N-diisopropylethylamine / CH2Cl2 / 19 h / Ambient temperature 4: 1.) ozone, 2.) Me2S / 1a.) CH2Cl2, -78 deg C, 0.5 h, 1b.) RT, O.5 h, 2.) RT, 1 h 5: pyridinium dichromate / dimethylformamide / 17 h / Ambient temperature 6: dimethylformamide; H2O; diethyl ether / 1 h / Ambient temperature 7: 72 percent / ZnBr2 / CH2Cl2 / 3 h / Ambient temperature 8: 96 percent / aq. NaOH / propan-2-ol / 0.5 h / 60 °C 9: 48 percent / benzenesulfonyl chloride, pyridine 10: 44 percent / Zn, dibromoethane / tetrahydrofuran / 1.12 h / Heating 11: 30 percent / SOCl2, pyridine / CH2Cl2 / 0.08 h / Heating 12: 76 percent / 50percent aq. HF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 90 percent / DIBAH / toluene / 0.5 h / -78 °C 4: 79 percent / N,N-diisopropylethylamine / CH2Cl2 / 19 h / Ambient temperature 5: 1.) ozone, 2.) Me2S / 1a.) CH2Cl2, -78 deg C, 0.5 h, 1b.) RT, O.5 h, 2.) RT, 1 h 6: pyridinium dichromate / dimethylformamide / 17 h / Ambient temperature 7: dimethylformamide; H2O; diethyl ether / 1 h / Ambient temperature 8: 72 percent / ZnBr2 / CH2Cl2 / 3 h / Ambient temperature 9: 96 percent / aq. NaOH / propan-2-ol / 0.5 h / 60 °C 10: 48 percent / benzenesulfonyl chloride, pyridine 11: 44 percent / Zn, dibromoethane / tetrahydrofuran / 1.12 h / Heating 12: 30 percent / SOCl2, pyridine / CH2Cl2 / 0.08 h / Heating 13: 76 percent / 50percent aq. HF / tetrahydrofuran / 18 h / Ambient temperature View Scheme