1: 1) n-BuLi / 1) THF, -30 deg C, 2 h, 2) THF, -78 deg C, 2 h, then -78 dec C -> rt, 16 h 2: 97 percent / tetrahydrofuran / 4 h / Heating 3: 39 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 4: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 5: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

1: 97 percent / tetrahydrofuran / 4 h / Heating 2: 39 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 3: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 4: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

1: 39 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 2: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 3: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

1: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 2: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

zinc(II) tetrahydroborate in diethyl ether 1) 0 deg C, 3 h, 2) rt, 24 h;

1: 46 percent / n-BuLi 2: 97 percent / tetrahydrofuran / Heating 3: 37 percent / LDA / tetrahydrofuran 4: H2 / H2PtO2 5: Zn(BH4)2 / diethyl ether View Scheme

1: 65 percent / aq. HBr / petroleum ether / 65 h / 90 - 95 °C 2: 95 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / Ambient temperature 3: 1) n-BuLi / 1) THF, -30 deg C, 2 h, 2) THF, -78 deg C, 2 h, then -78 dec C -> rt, 16 h 4: 97 percent / tetrahydrofuran / 4 h / Heating 5: 39 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 6: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 7: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / Ambient temperature 2: 1) n-BuLi / 1) THF, -30 deg C, 2 h, 2) THF, -78 deg C, 2 h, then -78 dec C -> rt, 16 h 3: 97 percent / tetrahydrofuran / 4 h / Heating 4: 39 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 5: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 6: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme

1: 1) n-BuLi / 1) THF, -30 deg C, 2 h, 2) THF, -78 deg C, 2 h, then -78 dec C -> rt, 16 h 2: 97 percent / tetrahydrofuran / 4 h / Heating 3: 39 percent / LDA / tetrahydrofuran; hexane / 5 h / 0 deg C -> 25 deg C 4: 98 percent / H2 / Pt / ethyl acetate / 48 h / 760 Torr 5: 48 percent / Zn(BH4)2 / diethyl ether / 1) 0 deg C, 3 h, 2) rt, 24 h View Scheme