1.1: 95.1 percent / mCPBA 2.1: 46.4 percent / (R,R)-salenCo(III)OAc / H2O / 72 h / 10 - 20 °C 3.1: 99 percent / H2 / Pd/C; Co(OAc)4 / methanol / 20 °C / 760 Torr 4.1: TMSOTf / CH2Cl2; petroleum ether / 2 h 5.1: 2.70 g / NaOMe / methanol / 3 h / 20 °C 6.1: 73.3 percent / DMAP; Et3N / CH2Cl2 / 20 °C 7.1: 86.1 percent / dimethylsulfoxide / 20 °C 8.1: 72.4 percent / cateholborane / 36 h / 20 °C 9.1: 95.4 percent / I2; aq. NaOH / diethyl ether / 0.33 h / 20 °C 10.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 10.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 10.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 11.1: 131 mg / (S)-2-methyl-CBS-oxazaborolidine; BH3*Me2S / tetrahydrofuran; toluene / 0.25 h / 0 °C 12.1: 96.4 percent / diethyl ether / 1 h / 0 °C 13.1: 72 percent / Li-naphthalene / tetrahydrofuran / -25 °C 14.1: MnO2 / CH2Cl2 / 3 h / Heating 15.1: 33.6 mg / NaH2PO4; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O / 20 °C 16.1: NEt3; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 6 h 16.2: 81 percent / DMAP / tetrahydrofuran; toluene / Heating 17.1: 91 percent / aq. HCl / tetrahydrofuran; H2O / 48 h / 20 °C View Scheme

1: (i) O3, AcOH, (ii) Zn, H2O 2: O2 / Co(OAc)2 View Scheme

3-chloro-benzenecarboperoxoic acid

(S)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl; potassium fluoride; bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane; dihydrogen peroxide; potassium hydrogencarbonate 1.) 40 deg C, 24 h, 2.) THF, MeOH, RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;