1: 86 percent / H2 / PtO2 / ethyl acetate / 2327.2 Torr 2: KH, MeOH / diethyl ether / 4 h / Heating 3: oxalyl chloride, DMF / acetonitrile / 1.) 0 deg C, 15 min, 2.) -22 deg C, 15 min 4: NH3 / acetonitrile; tetrahydrofuran / 1 h / -76 - 20 °C 5: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 2585.7 Torr 6: 18 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / tetrahydrofuran / 24 h 7: KOH / H2O; tetrahydrofuran / 0.5 h 8: 63 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 12 h / Heating 9: O2 / Irradiation View Scheme

1.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h / 40 °C 1.2: 3 h / 40 °C 2.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; (R,R)-Ts-DENEBTM / methanol / 70 h / 60 °C View Scheme

hydrogenchloride

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