1: catechol borane, (S)-oxazaborolidine catalyst 3: OsO4, R3NO 4: H+ 5: 1.) n-BuLi, 2.) CuI(Ph3P)2 6: p-TsOH / methanol / Ambient temperature 7: NaIO4 8: NaCNBH3 9: 5percent ZnI2 / ethanol / 60 °C 10: 60 percent / 10percent Pd(OCOCF3)2(PPh3)2, 1,2,2,6,6-pentamethylpiperidine / toluene / 120 °C 11: 79 percent / BF3*OEt2 / various solvent(s) 12: 60 percent / camphorsulfonic acid, 3,5-dinitroperoxybenzoic acid / CH2Cl2 / 0 °C 13: 86 percent / TPAP, NMO 14: 80 percent / H2 / Pd(OH)2 View Scheme