1: KOOCNNCOOK / methanol; acetic acid / 8 h / 0 °C 2: aq. KOH / tetrahydrofuran / 0 °C 3: 1.) D(-)-α-phenylglycinol, dicyclohexylcarbodiimide, 2.) aq. HCl / 1.) CH3CN, 2.) 65 deg C, 3 h 4: 75 percent / DBU / CH2Cl2 / 2 h / Heating 5: 70 percent / 2,6-di-tert-butyl-4-methylphenol / toluene / 14 h / 125 °C 6: 1.) MCPBA, 2.) trimethylphosphite / 1.) CH2Cl2, -78 deg C, 2.) MeOH, reflux, 2.5 h 7: 93 percent / DEAD, Ph3P / tetrahydrofuran / 0.25 h 8: 85 percent / NaOMe / methanol / 2.5 h 9: 1.) Ac2O, Et3N, DMAP / 1.) CH2Cl2, 2.) -10 deg C 10: LiAlH4 / diethyl ether / 30 h / 0 °C 11: potassium hydride / toluene / 3 h / Heating 12: DMAP, Et3N / CH2Cl2 / 16 h / Ambient temperature 13: 1.) aq. HCl, 2.) Ag2CO3 / 1.) THF, 45 deg C, 2.) benzene, reflux, 4 h 14: 31 percent / BBr3 / CH2Cl2 / 6 h / -23 °C View Scheme

1.1: zinc; HCl / ethanol 1.2: diisopropylethylamine 2.1: potassium hexamethyldisilazide / tetrahydrofuran / -50 - 25 °C View Scheme