1: TBAF / tetrahydrofuran 2: (COCl)2; DMSO; Et3N 4: (COCl)2; DMSO; Et3N 6: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 7: Ph3P; H2O 8: Et3N 9: 70 percent / 1,2-dichloro-benzene / Heating 10: LiOH 12: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 13: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 14: HCl View Scheme

1.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C 2.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 3.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 3.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 3.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 4.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 5.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 6.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 7.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 8.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 9.1: 60 percent / various solvent(s) / 66 h / Heating 10.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 11.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 12.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 13.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 14.1: HCl / diethyl ether / 1 h / 20 °C 14.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme