1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C 3.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 5.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 7.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 7.2: 0.5 h / 20 °C 8.1: sodium tetrahydroborate / methanol / 20 °C 9.1: boron tribromide / dichloromethane / 0.17 h / 20 °C View Scheme

1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C 3.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 5.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 7.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 7.2: 0.5 h / 20 °C 8.1: sodium tetrahydroborate / methanol / 20 °C View Scheme

1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C 3.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 5.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 7.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 7.2: 0.5 h / 20 °C View Scheme

Multi-step reaction with 5 steps 1.1: ozone / toluene / 0 °C1.2: 0.5 h / 20 °C1.3: 2 h / 80 °C2.1: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 0.05 h / 0 °C2.2: 0.5 h / 20 °C3.1: pyridine / 1 h / 20 °C4.1: lipase AK / tetrahydrofuran; water / 24 h / 20 °C / pH 7.41 / aq. phosphate buffer; Enzymatic reaction4.2: 0.5 h / 0 °C5.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran / -40 - 0 °C  

Multi-step reaction with 2 steps 1.1: lipase AK / tetrahydrofuran; water / 24 h / 20 °C / pH 7.41 / aq. phosphate buffer; Enzymatic reaction1.2: 0.5 h / 0 °C2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran / -40 - 0 °C