1.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C 2.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C 3.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C 4.1: p-toluenesulfonic acid; trimethyl orthoformate 4.2: 89 percent / HCl / acetone 5.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C 6.1: nBuLi / tetrahydrofuran / -20 °C 6.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C 7.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C 8.1: 97 percent / HCl / acetone; H2O 9.1: LDA / tetrahydrofuran / 0.17 h / -20 °C 9.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C 10.1: HBr / CH2Cl2 / 0 °C 11.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C 12.1: 55 percent / various solvent(s) / 20 h / 63 °C View Scheme

1.1: 88 percent / mCPBA / ethyl acetate / 20 °C 2.1: 93 percent / nBuLi; DIPA / tetrahydrofuran / 20 °C 3.1: 77 percent / p-TsOH / toluene / Heating 4.1: Dibal-H / petroleum ether; hexane / 0.5 h / -60 - 20 °C 4.2: 92 percent / SiO2 / H2O; toluene / 1 h / -20 - 0 °C View Scheme

sulfuric acid in nitromethane T=0°C; Cyclization; 0.5 h; Title compound not separated from byproducts.;

phosphoric acid in toluene T=110°C; 8 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1.1: NaH / tetrahydrofuran / 0 - 20 °C 1.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C 2.1: 86 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C View Scheme

1.1: 70 percent / diethyl ether / 1 h / 0 °C 2.1: NaH / tetrahydrofuran / 0 - 20 °C 2.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C 3.1: 86 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C View Scheme

1: 1) lithium diisopropyl amide / 1) THF, a) -78 deg C, 100 min, b) 10 deg C, 60 min, 2) 40 min 2: KOH; ethanol / 4 h 3: nBu4NCN / 8 h / 75 °C 4: 45 percent / ozone, sodium bicarbonate / ethyl acetate / 8 h / 0 °C 5: 92 percent / NaBH4 / ethanol / 1.5 h / Ambient temperature 6: conc. HCl / CH2Cl2 / 31 h 7: AIBN, tri-n-butyltin hydride / toluene / 2 h / Heating 8: 93 percent / ozone / ethyl acetate / 0.5 h / -78 °C 9: SOCl2 / methanol / 2 h 10: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.08 h 11: 92 percent / PBr3 / petroleum ether / 1 h / 0 °C 12: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme

1: sodium bisulphate / H2O / 6 h / 0 - 15 °C 2: SOCl2, pyridine / benzene / 1 h / Heating 3: 1.8548 g / benzoyl peroxide, N-bromosuccinimide / CCl4 / 0.67 h / Heating 4: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme

1: 1.8548 g / benzoyl peroxide, N-bromosuccinimide / CCl4 / 0.67 h / Heating 2: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme

1: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.08 h 2: 92 percent / PBr3 / petroleum ether / 1 h / 0 °C 3: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme