1: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C 2: Br2 / CH2Cl2 / 0.17 h / -70 °C 3: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C 4: imidazole / dimethylformamide / 5 h / Ambient temperature 5: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 6: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 7: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 deg C, 18h 8: 85 percent / n-Bu4NF / tetrahydrofuran / 17 h / Ambient temperature View Scheme

1: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C 2: Br2 / CH2Cl2 / 0.17 h / -70 °C 3: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C 4: imidazole / dimethylformamide / 5 h / Ambient temperature 5: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 6: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 7: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 8: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1.1: t-BuOOH; Ti(OPr)4; D-(-)-DIPT 1.2: Br2 / -78 °C 1.3: TBAF / tetrahydrofuran / -78 °C 2.1: imidazole 3.1: tetrahydrofuran / 20 °C 4.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C 2: Br2 / CH2Cl2 / 0.17 h / -70 °C 3: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C 4: imidazole / dimethylformamide / 5 h / Ambient temperature 5: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 6: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 7: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 8: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

Stage #1: With  titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate kinetic resolution; Stage #2: With  bromine T=-78°C; Bromination; Stage #3: With  tetrabutyl ammonium fluoride in  tetrahydrofuran T=-78°C; Hydrolysis; desilylation;  Further stages.;   

Multi-step reaction with 2 steps 1.1: t-BuOOH; Ti(OPr)4; D-(-)-DIPT1.2: Br2 / -78 °C1.3: TBAF / tetrahydrofuran / -78 °C2.1: imidazole  

Multi-step reaction with 5 steps 1: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C2: Br2 / CH2Cl2 / 0.17 h / -70 °C3: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C4: imidazole / dimethylformamide / 5 h / Ambient temperature5: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature  

Multi-step reaction with 6 steps 1: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C2: Br2 / CH2Cl2 / 0.17 h / -70 °C3: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C4: imidazole / dimethylformamide / 5 h / Ambient temperature5: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature6: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min