trimethylsilyl iodide in acetonitrile T=-10°C; 0.333333 h;

disodium hydrogenphosphate; sodium amalgam in methanol T=-40°C; 0.166667 h;

1: 92 percent / DIBAL / CH2Cl2 / -78 °C 2: 87 percent / PPTS / methanol 3: 96 percent / Bu4NF / tetrahydrofuran 4: 1.) BuLi / 1.) THF, -78 deg C 5: toluene / Irradiation 6: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 7: 79 percent / NaH / tetrahydrofuran 8: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux 9: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

1: 1.) BuLi / 1.) THF, -78 deg C 2: toluene / Irradiation 3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 4: 79 percent / NaH / tetrahydrofuran 5: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux 6: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

1: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 2: 79 percent / NaH / tetrahydrofuran 3: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux 4: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

1: 87 percent / PPTS / methanol 2: 96 percent / Bu4NF / tetrahydrofuran 3: 1.) BuLi / 1.) THF, -78 deg C 4: toluene / Irradiation 5: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 6: 79 percent / NaH / tetrahydrofuran 7: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux 8: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

1: 96 percent / Bu4NF / tetrahydrofuran 2: 1.) BuLi / 1.) THF, -78 deg C 3: toluene / Irradiation 4: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 5: 79 percent / NaH / tetrahydrofuran 6: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux 7: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

ethyl ether hydrochloride in ethanol T=50°C;

1.1: 100 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C 2.1: Mg / tetrahydrofuran / 0.83 h / 20 °C 2.2: 73 percent / TMEDA / tetrahydrofuran / 1.5 h / -78 °C 3.1: BF3*OEt2; Ph3SiH / CH2Cl2 / 2.5 h / -78 - 20 °C 3.2: DIBAL-H / toluene / 3 h / -78 °C 3.3: 826 mg / Cs2CO3 / toluene; propan-2-ol / 17 h / 20 °C 4.1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C 5.1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h 6.1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C 7.1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 8.1: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme

1.1: Mg / tetrahydrofuran / 0.83 h / 20 °C 1.2: 73 percent / TMEDA / tetrahydrofuran / 1.5 h / -78 °C 2.1: BF3*OEt2; Ph3SiH / CH2Cl2 / 2.5 h / -78 - 20 °C 2.2: DIBAL-H / toluene / 3 h / -78 °C 2.3: 826 mg / Cs2CO3 / toluene; propan-2-ol / 17 h / 20 °C 3.1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C 4.1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h 5.1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C 6.1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 7.1: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme