water; 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=20°C; 1 h;

1.1: 88 percent / imidazole / dimethylformamide / 10 h / 20 °C 2.1: O3 / CH2Cl2 / 0.03 h / -78 °C 2.2: 83 percent / PPh3 / CH2Cl2 / 4 h / 20 °C 3.1: Zn(OTf)2; Et3N; (+)-N-methylephedrine / toluene / 18 h / 20 °C 4.1: 4.44 g / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 5.1: 85 percent / K2CO3; 18-crown-6 / toluene / 26 h / Heating 6.1: 93 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 7.1: 56 percent / EtMgBr; i-PrOH / CH2Cl2 / 39 h / 0 - 20 °C 8.1: 87 percent / diethylisopropylamine / CH2Cl2 / 0.42 h / 0 °C 9.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 10.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 11.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 12.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 13.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 14.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 15.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 16.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 17.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 18.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 19.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 20.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 21.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 22.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 23.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 24.1: 2,4,6-trichlorobenzoyl chloride; Et3N 24.2: 74 percent / 4-dimethylaminopyridine 25.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 26.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 1.2: 90 percent / Et3N / CH2Cl2 / -78 - 0 °C 2.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C 3.1: 99 percent / pTSA*H2O / dioxane; H2O / 2 h / 50 °C 4.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C 5.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C 6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 6.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 7.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 8.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 9.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 10.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 11.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 12.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 13.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1.1: 98 percent / 2,6-lutidine / CH2Cl2 / 0 °C 2.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 20 °C 3.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 3.2: 90 percent / Et3N / CH2Cl2 / -78 - 0 °C 4.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C 5.1: 99 percent / pTSA*H2O / dioxane; H2O / 2 h / 50 °C 6.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C 7.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C 8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 8.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 9.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 10.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 11.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 12.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 13.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 14.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 15.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: 99 percent / pTSA*H2O / dioxane; H2O / 2 h / 50 °C 3.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C 4.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C 5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 5.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 6.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 7.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 8.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 9.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 10.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 11.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 12.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 20 °C 2.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 2.2: 90 percent / Et3N / CH2Cl2 / -78 - 0 °C 3.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C 4.1: 99 percent / pTSA*H2O / dioxane; H2O / 2 h / 50 °C 5.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C 6.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C 7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 7.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 8.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 10.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 11.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 12.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 13.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 14.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 2: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C 3: 62 percent / Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme

3,3-dimethyldioxirane in dichloromethane; acetone T=0°C;

1.1: TiCl4 / CH2Cl2 / -78 °C 2.1: CSA / benzene / 20 °C 3.1: 91 percent / LiAlH4 / diethyl ether / -78 °C 4.1: 93 percent / Et2Zn / diethyl ether / 20 °C 5.1: N-iodosuccinimide / 20 °C 6.1: n-Bu3SnH; AIBN / benzene / Heating 7.1: 97 percent / imidazole / dimethylformamide / 20 °C 8.1: 78 percent / TiCl4 / CH2Cl2 / -78 - -40 °C 9.1: 98 percent / 2,6-lutidine / CH2Cl2 / 0 °C 10.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 20 °C 11.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 11.2: 90 percent / Et3N / CH2Cl2 / -78 - 0 °C 12.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C 13.1: 99 percent / pTSA*H2O / dioxane; H2O / 2 h / 50 °C 14.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C 15.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C 16.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 16.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 17.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 18.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 19.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 20.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 21.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 22.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 23.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 1.2: Et3N / CH2Cl2 / -78 - 20 °C 2.1: diethyl ether / 0 - 20 °C 3.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH2Cl2 / 0 - 20 °C 4.1: n-BuLi / tetrahydrofuran / -78 °C 4.2: 97 percent / tetrahydrofuran / -78 - 20 °C 5.1: 64 percent / N-iodosuccinimide; AgNO3 / acetone 6.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether 7.1: 86 percent / PhSH; BF3*OEt2 / CH2Cl2 / 20 °C 8.1: 99 percent / pyridine; 4-DMAP / CH2Cl2 / 20 °C 9.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 9.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 10.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 11.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 12.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 13.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 14.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 15.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 16.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme