hydrogenchloride in tetrahydrofuran; methanol; water 0.666667 h;

acetic acid; zinc

dipotassium hydrogenphosphate; potassium dihydrogenphosphate; sodium chloride in tetrahydrofuran; water T=20°C; 0.25 - 0.5 h;

1: 10-deacetyl taxol(7α-OH) With 2-chloro-acetamide in tetrahydrofuran T=100°C; 3 h; 2: acetic anhydride in tetrahydrofuran T=100°C; 3 h; 3: With methanol; sodium hydrogencarbonate; thiourea T=20°C; 1 h; Product distribution / selectivity;

hydrogenchloride; ethanol T=0°C; 30 h;

1: 7-xylosyl-10-deacetyltaxol With sodium periodate; sulfuric acid in methanol; chloroform; water T=20°C; 3 h; 2: acetic anhydride With pyridine T=100°C; 0.5 h; 3: With acetic acid; phenylhydrazine in methanol T=50 - 60°C; 3 h;

4-(N,N-dimethlyamino)pyridine in dichloromethane T=20°C; 18 h; Inert atmosphereDarkness;

acetic acid; zinc in methanol T=60°C; 1 h;

1.1: 86 percent / pyridinium p-toluenesulfonate / benzene / 1 h / Heating 2.1: 100 percent / K2CO3 / tetrahydrofuran; methanol / 1 h / 20 °C 3.1: 100 percent / SmI2; methanol / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / 20 °C 4.1: TBAF; 2,6-di-t-butyl-4-hydroxytoluene / tetrahydrofuran / 3 h / 20 °C 4.2: 45 percent / sodium methoxide / methanol; tetrahydrofuran / 60 h / 20 °C 5.1: pyridine / CH2Cl2 / 0.25 h / 20 °C 6.1: 2,6-lutidine / CH2Cl2 / 12 h / -45 °C 7.1: 6.6 mg / aq. hydrogen peroxide; aq. Na2CO3 / ethyl acetate / 1 h / 20 °C 8.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 9.1: 97 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 0.08 h / 20 °C 10.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C 10.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 11.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C 12.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C 13.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH2Cl2 / 0.05 h / 20 °C 14.1: 80 percent / lithium diisopropyl amide; MoO5*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C 15.1: 92 percent / DMAP / CH2Cl2 / 0.5 h / 20 °C 16.1: 68 percent / DBN / toluene / 10 h / Heating 17.1: 86 percent / OsO4; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C 18.1: 86 percent / DBU / toluene / 4 h / Heating 19.1: pyridinium p-toluenesulfonic acid / methanol / 0.5 h / 20 °C 20.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C 21.1: 97 percent / H2 / Pd(OH)2 / ethanol / 1 h / 20 °C 22.1: 94 percent / pyridine / CH2Cl2 / 1 h / -78 - 0 °C 23.1: 66 percent / DMAP / CH2Cl2 / 6 h / 20 °C 24.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C 25.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C 26.1: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 27.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C 28.1: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 29.1: 84 percent / Zn; aq. AcOH / 16 h / 20 °C View Scheme

1.1: TBAF; 2,6-di-t-butyl-4-hydroxytoluene / tetrahydrofuran / 3 h / 20 °C 1.2: 45 percent / sodium methoxide / methanol; tetrahydrofuran / 60 h / 20 °C 2.1: pyridine / CH2Cl2 / 0.25 h / 20 °C 3.1: 2,6-lutidine / CH2Cl2 / 12 h / -45 °C 4.1: 6.6 mg / aq. hydrogen peroxide; aq. Na2CO3 / ethyl acetate / 1 h / 20 °C 5.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 6.1: 97 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 0.08 h / 20 °C 7.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C 7.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 8.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C 9.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C 10.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH2Cl2 / 0.05 h / 20 °C 11.1: 80 percent / lithium diisopropyl amide; MoO5*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C 12.1: 92 percent / DMAP / CH2Cl2 / 0.5 h / 20 °C 13.1: 68 percent / DBN / toluene / 10 h / Heating 14.1: 86 percent / OsO4; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C 15.1: 86 percent / DBU / toluene / 4 h / Heating 16.1: pyridinium p-toluenesulfonic acid / methanol / 0.5 h / 20 °C 17.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C 18.1: 97 percent / H2 / Pd(OH)2 / ethanol / 1 h / 20 °C 19.1: 94 percent / pyridine / CH2Cl2 / 1 h / -78 - 0 °C 20.1: 66 percent / DMAP / CH2Cl2 / 6 h / 20 °C 21.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C 22.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C 23.1: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 24.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C 25.1: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 26.1: 84 percent / Zn; aq. AcOH / 16 h / 20 °C View Scheme