sodium hydroxide in methanol T=0°C;

1: 1) NaH / 1) THF 2: NaBH4 / methanol / -25 °C 3: 65percent aq. acetic acid / tetrahydrofuran / 50 °C 4: 94 percent / imidazole / dimethylformamide / 23 °C 5: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 6: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 7: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: 1) NaH / 1) THF 2: NaBH4 / methanol / -25 °C 3: 65percent aq. acetic acid / tetrahydrofuran / 50 °C 4: 94 percent / imidazole / dimethylformamide / 23 °C 5: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 6: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 7: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: SO3*pyridine, triethylamine / dimethylsulfoxide / 0.5 h / 23 °C 2: 1) NaH / 1) THF 3: NaBH4 / methanol / -25 °C 4: 65percent aq. acetic acid / tetrahydrofuran / 50 °C 5: 94 percent / imidazole / dimethylformamide / 23 °C 6: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 7: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 8: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: 94 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 13 h / 23 °C 2: SO3*pyridine, triethylamine / dimethylsulfoxide / 0.5 h / 23 °C 3: 1) NaH / 1) THF 4: NaBH4 / methanol / -25 °C 5: 65percent aq. acetic acid / tetrahydrofuran / 50 °C 6: 94 percent / imidazole / dimethylformamide / 23 °C 7: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 8: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 9: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: 65percent aq. acetic acid / tetrahydrofuran / 50 °C 2: 94 percent / imidazole / dimethylformamide / 23 °C 3: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 4: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 5: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: NaBH4 / methanol / -25 °C 2: 65percent aq. acetic acid / tetrahydrofuran / 50 °C 3: 94 percent / imidazole / dimethylformamide / 23 °C 4: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 5: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 6: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 2: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 3: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: 94 percent / imidazole / dimethylformamide / 23 °C 2: 100 percent / H2 / (methyl benzoate)*Cr(CO)3 / acetone / 15 h / 120 °C / 51485.6 Torr 3: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 4: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme

1: 82 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 23 °C 2: 74 percent / 10percent aq. NaOH / methanol / 0 °C View Scheme