1: LDA / tetrahydrofuran / -78 up to -20 deg C 2: H2 / 5percent Pd/C / methanol 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 8: 72 percent / 48percent HBr View Scheme

1: LDA / tetrahydrofuran / -78 up to -20 deg C 2: H2 / 5percent Pd/C / methanol 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH View Scheme

1: LDA / tetrahydrofuran / -78 up to -20 deg C 2: H2 / 5percent Pd/C / methanol 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 8: 72 percent / 48percent HBr 9: 91 percent / CH2Cl2; propan-1-ol View Scheme