1: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 1 h / -78 °C 2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 4 h / 0 °C View Scheme

1: (R)-Ru(η6-mesitylene)-(S,S)-TsDPEN; sodium formate; N-hexadecyl-N,N,N-trimethylammonium bromide; sodium hydrogencarbonate / dichloromethane; water / 24 h / 20 °C 2: N-bromosuccinmide; water; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran / 1 h / 0 °C 3: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / -78 - -30 °C / Inert atmosphere 4: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / tetrahydrofuran; dichloromethane / 6 h / 0 °C / Inert atmosphere 5: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 1 h / -78 °C 6: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 4 h / 0 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / -78 - -30 °C / Inert atmosphere 2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / tetrahydrofuran; dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 1 h / -78 °C 4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 4 h / 0 °C View Scheme

1: N-bromosuccinmide; water; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran / 1 h / 0 °C 2: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / -78 - -30 °C / Inert atmosphere 3: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / tetrahydrofuran; dichloromethane / 6 h / 0 °C / Inert atmosphere 4: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 1 h / -78 °C 5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 4 h / 0 °C View Scheme

1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / dichloromethane / 8 h / 0 °C 2: sodium tetrahydroborate; cerium(III) chloride / methanol / 4 h / -78 °C 3: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 0 °C View Scheme

1.) Fetizons reagent Yield given. Multistep reaction;