1.1: sodium periodate; osmium(VIII) oxide / 0 - 20 °C 2.1: dicyclohexyl(trifluoromethylsulfonyloxy)borane; triethylamine / -78 - 0 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / tetrahydrofuran; water / 0.25 h 3.2: Acidic aq. solution 4.1: water; lithium hydroxide hydrate / 1,4-dioxane / 120 h / 40 °C 5.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.33 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 65 °C 7.1: 1.5 h / 65 °C 8.1: 2-hydroxy-pyridine / tert-butyl methyl ether / 65 °C View Scheme

1.1: sodium ethanolate; sodium iodide / ethanol 2.1: potassium acetate / water; dimethyl sulfoxide 3.1: sodium hydroxide 4.1: thionyl chloride 5.1: pyridine / 12 h / 40 °C 6.1: dicyclohexyl(trifluoromethylsulfonyloxy)borane; triethylamine / -78 - 0 °C 7.1: dihydrogen peroxide; lithium hydroxide hydrate / tetrahydrofuran; water / 0.25 h 7.2: Acidic aq. solution 8.1: water; lithium hydroxide hydrate / 1,4-dioxane / 120 h / 40 °C 9.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.33 h / 20 °C 10.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 65 °C 11.1: 1.5 h / 65 °C 12.1: 2-hydroxy-pyridine / tert-butyl methyl ether / 65 °C View Scheme

10 palladium on activated charcoal; hydrogen

1: (1S,2S,4S)-4-(2-carbamoyl-2-methylpropyl- carbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methylbutyl}-5-methylhexyl-carbamic acid benzyl ester With palladium 10 on activated carbon; hydrogen in isopropyl alcohol T=20°C; P=760.051 Torr; 2: (2E)-but-2-enedioic acid in ethanol