1: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; caesium carbonate / tetrahydrofuran / |Reflux 2: tetrabutyl ammonium fluoride / tetrahydrofuran 3: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 5: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 6: sodium hydride / tetrahydrofuran / 0 °C 7: o-hydroxynitrobenzene / 144 h / 130 °C / |Inert atmosphere 8: sodium hydroxide / methanol; water / 80 °C 9: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 10: Dess-Martin periodane / dichloromethane 11: boron trifluoride diethyl etherate / dichloromethane / 3 h / -10 °C 12: diphenylchlorosilane; indium(III) chloride / 1,2-dichloro-ethane / 21 h / |Reflux 13: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 14: (1S)-10-camphorsulfonic acid / tetrahydrofuran / |Reflux 15: lithium aluminium tetrahydride / 1,4-dioxane / |Reflux 16: Dess-Martin periodane / dichloromethane / 2.5 h / 0 - 20 °C View Scheme

1: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; caesium carbonate / tetrahydrofuran / |Reflux 2: tetrabutyl ammonium fluoride / tetrahydrofuran 3: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 5: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 6: sodium hydride / tetrahydrofuran / 0 °C 7: o-hydroxynitrobenzene / 144 h / 130 °C / |Inert atmosphere 8: sodium hydroxide / methanol; water / 80 °C 9: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 10: Dess-Martin periodane / dichloromethane 11: boron trifluoride diethyl etherate / dichloromethane / 3 h / -10 °C 12: diphenylchlorosilane; indium(III) chloride / 1,2-dichloro-ethane / 21 h / |Reflux 13: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 14: (1S)-10-camphorsulfonic acid / tetrahydrofuran / |Reflux 15: Dess-Martin periodane / dichloromethane / 5.5 h / 0 - 20 °C 16: lithium aluminium tetrahydride / 1,4-dioxane / 6 h / |Reflux View Scheme