1: With borane dimethyl sulfide complex in tetrahydrofuran T=0 - 20°C; 12 h; Inert atmosphere; 2: With water in tetrahydrofuran; methanol T=0°C; 0.5 h;

hydrogen; palladium on activated charcoal

1: (i) CaSO4, (ii) NaI, (iii) /BRN= 610776/ 2: (i) NaOMe, (ii) /BRN= 773692/ 3: (saponification) 4: H2 / Pd-C View Scheme

1: (saponification) 2: H2 / Pd-C View Scheme

1: (i) NaOMe, (ii) /BRN= 773692/ 2: (saponification) 3: H2 / Pd-C View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 3.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 4.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux View Scheme

palladium on activated charcoal; ethanol Hydrogenation;

hydrogenchloride; amalgamated zinc

1: methanol. KOH-solution 2: aqueous hydrochloric acid; amalgamated zinc View Scheme

1: ethanol / und Erhitzen des Reaktionsprodukts mit wss.Kalilauge und anschliessend mit wss.Schwefelsaeure 2: methanol; sodium / Elektrolyse des Reaktionsgemisches und anschliessende Behandlung mit wss.-aethanol.Kalilauge View Scheme