1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 40 °C / |Inert atmosphere 2.1: potassium hexacyanoferrate(III); methanesulfonamide; K2OsO4*2H2O; sodium hydrogencarbonate; potassium carbonate; (DHQD)2Pyr / water; tert-butyl alcohol / 72 h / 0 °C 3.1: sulfuric acid / 3 h / 80 °C 4.1: tetrahydrofuran / 1 h / -78 - -70 °C 5.1: hydrogenchloride / methanol / 14 h / 20 °C 6.1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / 0.75 h / |Reflux 7.1: silver perchlorate / tetrahydrofuran / 20 °C / |Inert atmosphere 8.1: toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 0 - 20 °C 9.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 9.2: -78 - 20 °C / |Inert atmosphere 10.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 11.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

1.1: sulfuric acid / 3 h / 80 °C 2.1: tetrahydrofuran / 1 h / -78 - -70 °C 3.1: hydrogenchloride / methanol / 14 h / 20 °C 4.1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / 0.75 h / |Reflux 5.1: silver perchlorate / tetrahydrofuran / 20 °C / |Inert atmosphere 6.1: toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 0 - 20 °C 7.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 7.2: -78 - 20 °C / |Inert atmosphere 8.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 9.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

sodium hydroxide; sodium dithionite; air 1) H2O, 2 h, reflux, 2) MeOH, RT, 20 min; Yield given. Multistep reaction;