1: 4-(N,N-dimethlyamino)pyridine; triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h / 0 - 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere View Scheme

Multi-step reaction with 12 steps 1.1: sodium periodate adsorbed on silica gel / dichloromethane / 20 °C / Inert atmosphere2.1: benzene / 39 h / Inert atmosphere; Reflux3.1: (4R,5R)-Ph2-1,3-Me2-2-oxo-2-(CH2)5N-1,3,2-diazaphospholidine / dichloromethane / 4 h / -78 °C / Inert atmosphere3.2: 0.25 h / 0 °C4.1: triethylamine / dichloromethane / 3 h / -30 - 20 °C / Inert atmosphere5.1: [Au(1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene)(NCPh)]+SbF6- / dichloromethane / 10 h / 20 °C / Molecular sieve; Inert atmosphere6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere7.1: 4-(N,N-dimethlyamino)pyridine; 1H-imidazole / dichloromethane / 10 h / 20 °C / Inert atmosphere8.1: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / 2 h / Inert atmosphere9.1: n-butyllithium; tungsten hexachloride / hexane; tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere10.1: hydrogen / Crabtree-BArF catalyst, BArF = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate / dichloromethane / 96 h / 60006 Torr / Inert atmosphere11.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 4 h / 80 °C / Inert atmosphere12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere  

Multi-step reaction with 11 steps 1.1: benzene / 39 h / Inert atmosphere; Reflux2.1: (4R,5R)-Ph2-1,3-Me2-2-oxo-2-(CH2)5N-1,3,2-diazaphospholidine / dichloromethane / 4 h / -78 °C / Inert atmosphere2.2: 0.25 h / 0 °C3.1: triethylamine / dichloromethane / 3 h / -30 - 20 °C / Inert atmosphere4.1: [Au(1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene)(NCPh)]+SbF6- / dichloromethane / 10 h / 20 °C / Molecular sieve; Inert atmosphere5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere6.1: 4-(N,N-dimethlyamino)pyridine; 1H-imidazole / dichloromethane / 10 h / 20 °C / Inert atmosphere7.1: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / 2 h / Inert atmosphere8.1: n-butyllithium; tungsten hexachloride / hexane; tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere9.1: hydrogen / Crabtree-BArF catalyst, BArF = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate / dichloromethane / 96 h / 60006 Torr / Inert atmosphere10.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 4 h / 80 °C / Inert atmosphere11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere