1: 76 percent / LAH, EtOH / diethyl ether 2: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 4: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 5: 70 percent / LAH, EtOH / diethyl ether 6: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 76 percent / LAH, EtOH / diethyl ether 2: 80 percent / H2, quinoline / Lindlar's catalyst / hexane View Scheme

1: 76 percent / LAH, EtOH / diethyl ether 2: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 76 percent / LAH, EtOH / diethyl ether 2: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 4: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 5: 70 percent / LAH, EtOH / diethyl ether View Scheme

1: 76 percent / LAH, EtOH / diethyl ether 2: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 4: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 5: 70 percent / LAH, EtOH / diethyl ether View Scheme