1: 10percent aq. AcOH / acetone / 14 h / 25 °C 2: 5percent NaOMe / methanol / 2 h / 25 °C 3: Na / liquid ammonia / 0.5 h / -78 °C View Scheme

1: 30 percent / NaH, 18-crown-6 (3 equiv. each) / dimethylformamide / 18 h / 0 °C 2: 79 percent / trifluoroacetic acid / H2O / 3 h / 50 °C View Scheme

ammonia; sodium methylate; sodium 1) MeOH, 25 deg C, 2 h, 2) THF, -78 deg C, 30 min; Yield given. Multistep reaction;

1: 70 percent / imidazole / CH2Cl2 2: TPP; DIAD / tetrahydrofuran 3: NMO; OsO4 / acetone; tetrahydrofuran; H2O 4: pTSA / acetone 5: 86 percent / NH3 / methanol 6: PCC; Celite / CH2Cl2 7: NaBH4; CeCl3*7H2O / methanol 8: TPP; DIAD / tetrahydrofuran 9: TBAF / tetrahydrofuran 10: NH3 / methanol 11: aq. HCl / methanol View Scheme

1: TPP; DIAD / tetrahydrofuran 2: NMO; OsO4 / acetone; tetrahydrofuran; H2O 3: pTSA / acetone 4: 86 percent / NH3 / methanol 5: PCC; Celite / CH2Cl2 6: NaBH4; CeCl3*7H2O / methanol 7: TPP; DIAD / tetrahydrofuran 8: TBAF / tetrahydrofuran 9: NH3 / methanol 10: aq. HCl / methanol View Scheme

1: 86 percent / NH3 / methanol 2: PCC; Celite / CH2Cl2 3: NaBH4; CeCl3*7H2O / methanol 4: TPP; DIAD / tetrahydrofuran 5: TBAF / tetrahydrofuran 6: NH3 / methanol 7: aq. HCl / methanol View Scheme

1: TPP; DIAD / tetrahydrofuran 2: TBAF / tetrahydrofuran 3: NH3 / methanol 4: aq. HCl / methanol View Scheme

1: PCC; Celite / CH2Cl2 2: NaBH4; CeCl3*7H2O / methanol 3: TPP; DIAD / tetrahydrofuran 4: TBAF / tetrahydrofuran 5: NH3 / methanol 6: aq. HCl / methanol View Scheme

1: Pseudomonas cepacia lipase; NaOH / aq. phosphate buffer; acetone / pH 7.0 - 7.2 2: N-methylmorpholine N-oxide; OsO4; H2O / acetone / 24 h / 20 °C 3: 20.16 g / p-TSA / acetone / 20 h / 20 °C 4: 93 percent / KCN / methanol / 2 h / 20 °C 5: 76 percent / pyridinium chlorochromate; Celite / CH2Cl2 / 15 h / 20 °C 6: 84 percent / sodium borohydride; CeCl3*7H2O / methanol / 0.75 h / 0 °C 7: 72 percent / imidazole / dimethylformamide / 12 h / 20 °C 8: KOH; KMnO4; MgSO4 / methanol; H2O / 2 h / 0 °C 9: 710 mg / sodium borohydride / propan-2-ol / 1 h / 0 °C 10: 85 percent / pyridine / CH2Cl2 / 0 - 20 °C 11: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 12: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 55 °C 13: 980 mg / NH3 / methanol / 48 h / 110 °C 14: 84 percent / trifluoroacetic acid; H2O / 2 h / 20 °C View Scheme

1: N-methylmorpholine N-oxide; OsO4; H2O / acetone / 24 h / 20 °C 2: 20.16 g / p-TSA / acetone / 20 h / 20 °C 3: 93 percent / KCN / methanol / 2 h / 20 °C 4: 76 percent / pyridinium chlorochromate; Celite / CH2Cl2 / 15 h / 20 °C 5: 84 percent / sodium borohydride; CeCl3*7H2O / methanol / 0.75 h / 0 °C 6: 72 percent / imidazole / dimethylformamide / 12 h / 20 °C 7: KOH; KMnO4; MgSO4 / methanol; H2O / 2 h / 0 °C 8: 710 mg / sodium borohydride / propan-2-ol / 1 h / 0 °C 9: 85 percent / pyridine / CH2Cl2 / 0 - 20 °C 10: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 11: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 55 °C 12: 980 mg / NH3 / methanol / 48 h / 110 °C 13: 84 percent / trifluoroacetic acid; H2O / 2 h / 20 °C View Scheme