反应条件
<b>Multi-step reaction with 22 steps<br /> </b>1.1: 49 percent / salicylic acid; selenium dioxide; tert-butyl hydroperoxide / CH<sub>2</sub>Cl<sub>2</sub>; H<sub>2</sub>O / 24 h / 20 °C<br />2.1: 85 percent / triphenylphosphine; N-bromosuccinimide / CH<sub>2</sub>Cl<sub>2</sub> / 2 h / -20 °C<br />3.1: n-butyl lithium / tetrahydrofuran; hexane / 1.5 h / 0 - 20 °C<br />3.2: 81 percent / tetrahydrofuran; hexane / 3 h / -20 - 20 °C<br />4.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH<sub>2</sub>Cl<sub>2</sub>; decane / -20 °C<br />5.1: 95 percent / pyridine / CH<sub>2</sub>Cl<sub>2</sub> / 48 h / -10 °C<br />6.1: perchloric acid / tetrahydrofuran; H<sub>2</sub>O / 2 h / Heating<br />6.2: 67 percent / 2,6-lutidine / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / -20 °C<br />7.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH<sub>2</sub>Cl<sub>2</sub>; decane / 29 h / 20 °C<br />8.1: sodium iodide; 18-c-6 / butan-2-one / Heating<br />8.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating<br />9.1: 93 percent / triethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 3 h / -78 °C<br />10.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C<br />10.2: tetrahydrofuran; hexane / 0.5 h<br />11.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH<sub>2</sub>Cl<sub>2</sub> / 2 h / 20 °C<br />12.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C<br />13.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H<sub>2</sub>O; CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />14.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C<br />15.1: 4-dimethylaminopyridine / CH<sub>2</sub>Cl<sub>2</sub> <br />16.1: HCl / tetrahydrofuran / 5 h / 0 °C<br />17.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C<br />18.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating<br />19.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH<sub>2</sub>Cl<sub>2</sub> / 0.5 h / 20 °C<br />20.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h<br />20.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C<br />21.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H<sub>2</sub>O; CH<sub>2</sub>Cl<sub>2</sub> / 2 h / 0 °C<br />22.1: DMSO; oxalyl chloride; Et<sub>3</sub>N / CH<sub>2</sub>Cl<sub>2</sub> / 0.92 h / -78 °C<br /> <br />
参考文献
Lautens, Mark; Colucci, John T.; Hiebert, Sheldon; Smith, Nicholas D.; Bouchain, Giliane Organic Letters, 2002 , vol. 4, # 11 p. 1879 - 1882
