1: 1) LDA / 1) THF, -78 deg C, 15 min; -30 deg C, 1.5 h, 2) THF, -78 deg C, 15 min; -40 deg C, 1 h 2: 0.940 g / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h 3: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 4: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C View Scheme

bis(cyclopentadienyl)titanium dichloride; magnesium in tetrahydrofuran deoxygenation;

1.1: 68 percent / PPh3 / CH2Cl2 / 0.25 h / -60 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 65 percent / tetrahydrofuran / 6 h / -78 - 20 °C 3.1: 74 percent / 4 Angstroem molecular sieves; TBAF*3H2O / tetrahydrofuran / 3 h 4.1: 81 percent / DCC; DMAP / CH2Cl2 / 14 h / 20 °C 5.1: 80 percent / CH2Cl2 / [Mo{(t-Bu)(3,5-dimethylphenyl)N}3] / toluene / 8 h / 80 °C 6.1: 99 percent / quinoline; H2 / Lindlar catalyst / hexane; CH2Cl2 / 8 h / 20 °C 7.1: 79 percent / aq. HF / acetonitrile; diethyl ether / 8 h / 20 °C View Scheme

1.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 2.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 3.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 3.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 4.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 5.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 5.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 6.1: 99 percent / HF*pyridine / tetrahydrofuran View Scheme

1.1: 70 percent / DIBAL-H / CH2Cl2 / -78 °C 2.1: 90 percent / benzene / Heating 3.1: Bu3P(O); Et2AlCl; (S)-3,3'-(Ph2PO)2-1,1'-binaphthalene-2,2'-diol / CH2Cl2; hexane / 39 h / -40 °C 4.1: TFA / CH2Cl2; hexane / 1 h / 20 °C 5.1: 75 percent / H2SO4 / Heating 6.1: 99 percent / imidazole / dimethylformamide 7.1: 87 percent / DIBAL-H / toluene / -78 °C 8.1: tetrahydrofuran / -78 °C 9.1: tetrahydrofuran 10.1: 51 percent / HCO2NH4; Bu3P / Pd(OAc)2 / benzene / 50 °C 11.1: 89 percent / AcOH; H2O / tetrahydrofuran / 50 °C 12.1: 90 percent / [Ti(O-i-Pr)4]; i-PrMgCl / diethyl ether / -78 - -50 °C 13.1: 65 percent / I2 / CH2Cl2 14.1: 90 percent / NEt3; DMAP / CH2Cl2 15.1: 50 percent / 9-BBN; K3PO4 / [PdCl2(dppf)] / tetrahydrofuran; dimethylformamide; H2O / 60 °C 16.1: 84 percent / NaOH; H2O / methanol 17.1: 2,4,6-trichlorobenzoyl chloride; NEt3 / tetrahydrofuran 17.2: 88 percent / DMAP / toluene; tetrahydrofuran 18.1: 99 percent / HF*pyridine / tetrahydrofuran View Scheme

1.1: 85 percent / i-Pr2NEt / 1,2-dichloro-ethane / 55 °C 2.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 20 °C 3.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 3.2: Et3N / CH2Cl2 / -78 - 20 °C 4.1: diethyl ether / 0 - 20 °C 5.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH2Cl2 / 0 - 20 °C 6.1: n-BuLi / tetrahydrofuran / -78 °C 6.2: 97 percent / tetrahydrofuran / -78 - 20 °C 7.1: 64 percent / N-iodosuccinimide; AgNO3 / acetone 8.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether 9.1: 86 percent / PhSH; BF3*OEt2 / CH2Cl2 / 20 °C 10.1: 99 percent / pyridine; 4-DMAP / CH2Cl2 / 20 °C 11.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 11.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 12.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 13.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 14.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 15.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 16.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 17.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C View Scheme

1: LDA / tetrahydrofuran / -78 °C 2: RuBnCl2(PCy3)2 / benzene / 24 h / 20 °C 3: Dess-Martin periodinane / CH2Cl2 / 20 °C 4: NaBH4 / methanol; tetrahydrofuran / -78 - 20 °C 5: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 6: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 7: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 8: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C View Scheme

1.1: (CF3CO2)2IC6H5 / methanol; tetrahydrofuran / 20 °C 1.2: 95 percent / p-TsOH / dioxane; H2O / 50 °C 2.1: LDA / tetrahydrofuran / -78 °C 3.1: RuBnCl2(PCy3)2 / benzene / 24 h / 20 °C 4.1: Dess-Martin periodinane / CH2Cl2 / 20 °C 5.1: NaBH4 / methanol; tetrahydrofuran / -78 - 20 °C 6.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 7.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 8.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 9.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C View Scheme

1.1: thiocarbonyl diimidazole; 4-DMAP / tetrahydrofuran / 95 °C 1.2: n-Bu3SnH; AIBN / benzene / 1 h / 80 °C 2.1: (CF3CO2)2IC6H5 / methanol; tetrahydrofuran / 20 °C 2.2: 95 percent / p-TsOH / dioxane; H2O / 50 °C 3.1: LDA / tetrahydrofuran / -78 °C 4.1: RuBnCl2(PCy3)2 / benzene / 24 h / 20 °C 5.1: Dess-Martin periodinane / CH2Cl2 / 20 °C 6.1: NaBH4 / methanol; tetrahydrofuran / -78 - 20 °C 7.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 8.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 9.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 10.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C View Scheme

1: 100 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 2: Et3N / tetrahydrofuran / 0.83 h / 20 °C 3: polystyrene-supported DMAP / toluene / 2 h / 80 °C 4: 2.2 mg / polymer-supported TsOH / CH2Cl2 / 1 h / 20 °C View Scheme