lithium hydroxide in methanol; water T=20°C; 20 h;

1: With hydrogenchloride; water in tetrahydrofuran T=20°C; 18 h; 2: in tetrahydrofuran pH=6.8; Aqueous phosphate buffer;

1: With lithium hydroxide; water in tetrahydrofuran 16 h; 2: With hydrogenchloride in tetrahydrofuran; water

1: (4-carboxy-n-butyl)-triphenylphosphonium bromide With potassium tert-butylate in tetrahydrofuran T=0°C; 2: (1S,5R,6R,7R)-6-lt;(3S)-3-hydroxy-5-phenyl-1-pentylgt;-7(R)-hydroxy-2-oxabicyclolt;3.3.0gt;octan-3-ol in tetrahydrofuran T=-17°C; Wittig Reaction; 20 h; 3: With aminosulfonic acid in tert-butyl methyl ether; water pH=1.5 - 2.0;

lithium hydroxide in methanol; water 8 h;

hydrogenchloride; water in acetone T=0 - 25°C; pH=1 - 3;

1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 6: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h View Scheme

1: 1.) NaH, 2.) n-BuLi 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 6: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h View Scheme

1: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 2: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 3: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 4: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h View Scheme

1: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 2: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 3: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 4: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h View Scheme