1.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 1.2: CH2Cl2 / 3 h / -78 - 20 °C 2.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 3.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 4.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

lithium hydroxide in ethylene glycol dimethyl ether; water T=80°C; 7 h;

1.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C 2.1: 95 percent / pyridine / CH2Cl2 / 48 h / -10 °C 3.1: perchloric acid / tetrahydrofuran; H2O / 2 h / Heating 3.2: 67 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 °C 4.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH2Cl2; decane / 29 h / 20 °C 5.1: sodium iodide; 18-c-6 / butan-2-one / Heating 5.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating 6.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 7.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 7.2: tetrahydrofuran; hexane / 0.5 h 8.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 9.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 10.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 11.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 12.1: 4-dimethylaminopyridine / CH2Cl2 13.1: HCl / tetrahydrofuran / 5 h / 0 °C 14.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 15.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 16.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 17.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 17.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 18.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 19.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 20.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 20.2: CH2Cl2 / 3 h / -78 - 20 °C 21.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 22.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 23.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: tetrahydrofuran; hexane / 0.5 h 3.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 4.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 5.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 6.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 7.1: 4-dimethylaminopyridine / CH2Cl2 8.1: HCl / tetrahydrofuran / 5 h / 0 °C 9.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 10.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 11.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 12.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 12.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 13.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 14.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 15.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 15.2: CH2Cl2 / 3 h / -78 - 20 °C 16.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 17.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 18.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH2Cl2; decane / 29 h / 20 °C 2.1: sodium iodide; 18-c-6 / butan-2-one / Heating 2.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating 3.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 4.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 4.2: tetrahydrofuran; hexane / 0.5 h 5.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 6.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 7.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 8.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 9.1: 4-dimethylaminopyridine / CH2Cl2 10.1: HCl / tetrahydrofuran / 5 h / 0 °C 11.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 12.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 13.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 14.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 14.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 15.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 16.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 17.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 17.2: CH2Cl2 / 3 h / -78 - 20 °C 18.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 19.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 20.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 49 percent / salicylic acid; selenium dioxide; tert-butyl hydroperoxide / CH2Cl2; H2O / 24 h / 20 °C 2.1: 85 percent / triphenylphosphine; N-bromosuccinimide / CH2Cl2 / 2 h / -20 °C 3.1: n-butyl lithium / tetrahydrofuran; hexane / 1.5 h / 0 - 20 °C 3.2: 81 percent / tetrahydrofuran; hexane / 3 h / -20 - 20 °C 4.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C 5.1: 95 percent / pyridine / CH2Cl2 / 48 h / -10 °C 6.1: perchloric acid / tetrahydrofuran; H2O / 2 h / Heating 6.2: 67 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 °C 7.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH2Cl2; decane / 29 h / 20 °C 8.1: sodium iodide; 18-c-6 / butan-2-one / Heating 8.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating 9.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 10.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 10.2: tetrahydrofuran; hexane / 0.5 h 11.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 12.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 13.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 14.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 15.1: 4-dimethylaminopyridine / CH2Cl2 16.1: HCl / tetrahydrofuran / 5 h / 0 °C 17.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 18.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 19.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 20.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 20.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 21.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 22.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 23.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 23.2: CH2Cl2 / 3 h / -78 - 20 °C 24.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 25.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 26.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: n-butyl lithium / tetrahydrofuran; hexane / 1.5 h / 0 - 20 °C 1.2: 81 percent / tetrahydrofuran; hexane / 3 h / -20 - 20 °C 2.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C 3.1: 95 percent / pyridine / CH2Cl2 / 48 h / -10 °C 4.1: perchloric acid / tetrahydrofuran; H2O / 2 h / Heating 4.2: 67 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 °C 5.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH2Cl2; decane / 29 h / 20 °C 6.1: sodium iodide; 18-c-6 / butan-2-one / Heating 6.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating 7.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 8.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 8.2: tetrahydrofuran; hexane / 0.5 h 9.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 10.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 11.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 12.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 13.1: 4-dimethylaminopyridine / CH2Cl2 14.1: HCl / tetrahydrofuran / 5 h / 0 °C 15.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 16.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 17.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 18.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 18.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 19.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 20.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 21.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 21.2: CH2Cl2 / 3 h / -78 - 20 °C 22.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 23.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 24.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 85 percent / triphenylphosphine; N-bromosuccinimide / CH2Cl2 / 2 h / -20 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 1.5 h / 0 - 20 °C 2.2: 81 percent / tetrahydrofuran; hexane / 3 h / -20 - 20 °C 3.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C 4.1: 95 percent / pyridine / CH2Cl2 / 48 h / -10 °C 5.1: perchloric acid / tetrahydrofuran; H2O / 2 h / Heating 5.2: 67 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 °C 6.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH2Cl2; decane / 29 h / 20 °C 7.1: sodium iodide; 18-c-6 / butan-2-one / Heating 7.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating 8.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 9.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 9.2: tetrahydrofuran; hexane / 0.5 h 10.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 11.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 12.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 13.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 14.1: 4-dimethylaminopyridine / CH2Cl2 15.1: HCl / tetrahydrofuran / 5 h / 0 °C 16.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 17.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 18.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 19.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 19.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 20.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 21.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 22.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 22.2: CH2Cl2 / 3 h / -78 - 20 °C 23.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 24.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 25.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 86 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 2.1: diethyl ether / 2 h / -78 °C 3.1: 34 mg / Dess-Martin periodinane / CH2Cl2 / 3 h / 0 °C 4.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 4.2: CH2Cl2 / 3 h / -78 - 20 °C 5.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 6.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 7.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 92 percent / 4-dimethylaminopyridine / tetrahydrofuran / 1.5 h / 50 °C 2.1: 75 percent / Bu3SnH / AIBN / toluene / 1.17 h / Heating 3.1: 86 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 4.1: diethyl ether / 2 h / -78 °C 5.1: 34 mg / Dess-Martin periodinane / CH2Cl2 / 3 h / 0 °C 6.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 6.2: CH2Cl2 / 3 h / -78 - 20 °C 7.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 8.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 9.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme