1: tBuLi 2: nBuLi, I2 3: 63 percent / Et3SiH / trifluoroacetic acid 4: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 5: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 6: 47 percent / ICl 7: 72 percent / aq. HI 8: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 9: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: nBuLi, I2 2: 63 percent / Et3SiH / trifluoroacetic acid 3: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 4: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 5: 47 percent / ICl 6: 72 percent / aq. HI 7: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 8: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

hexamethyl-distannane in benzene T=70°C; Irradiation;

1: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 2: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 3: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 4: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 5: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 2: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 3: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 2: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 3: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 4: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 2: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

carboxylesterase T=37°C; pH=7.4; 0.0833333 h;

1.1: anhydrous iron chloride / ethanol / 15 h / 20 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere 4.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; Pearlman's catalyst; hydrogen / methanol; water / 12 h / 30 °C / 760.05 Torr 6.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 7.1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere 8.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 9.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 9.2: -78 °C / Inert atmosphere 10.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 11.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 11.2: 1 h / 20 °C / Inert atmosphere 12.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 13.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 14.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme