methanol; sodium tetrahydroborate T=-78 - 25°C; 1.16667 h;

aluminum trihydride in tetrahydrofuran T=0°C; 1.5 h;

1.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C 2.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating 3.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 4.1: AgOTf / CH2Cl2 / 1 h / 25 °C 4.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 5.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 6.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 7.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 8.1: 99 percent / HCl; methanol / 16 h / 25 °C 9.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 9.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 10.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 11.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 12.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 13.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1.1: 98 percent / Dess-Martin periodane / CH2Cl2 / 2 h / 23 °C 2.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C 3.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating 4.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 5.1: AgOTf / CH2Cl2 / 1 h / 25 °C 5.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 6.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 7.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 8.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 9.1: 99 percent / HCl; methanol / 16 h / 25 °C 10.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 10.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 11.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 12.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 13.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 14.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1.1: m-CPBA / CH2Cl2 / 0.25 h / 23 °C 1.2: 91 percent / triethylamine / CH2Cl2 / 17 h / 40 °C 2.1: 98 percent / Dess-Martin periodane / CH2Cl2 / 2 h / 23 °C 3.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C 4.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating 5.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 6.1: AgOTf / CH2Cl2 / 1 h / 25 °C 6.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 7.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 8.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 9.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 10.1: 99 percent / HCl; methanol / 16 h / 25 °C 11.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 11.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 12.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 13.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 14.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 15.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating 2.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 3.1: AgOTf / CH2Cl2 / 1 h / 25 °C 3.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 4.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 5.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 6.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 7.1: 99 percent / HCl; methanol / 16 h / 25 °C 8.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 8.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 9.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 10.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 11.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 12.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 2.1: AgOTf / CH2Cl2 / 1 h / 25 °C 2.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 3.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 4.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 5.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 6.1: 99 percent / HCl; methanol / 16 h / 25 °C 7.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 7.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 8.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 9.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 10.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 11.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 2.1: 99 percent / HCl; methanol / 16 h / 25 °C 3.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 3.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 4.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 5.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 6.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 7.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1.1: AgOTf / CH2Cl2 / 1 h / 25 °C 1.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 2.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 3.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 4.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 5.1: 99 percent / HCl; methanol / 16 h / 25 °C 6.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 6.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 7.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 8.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 9.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 10.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 2.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 3.1: 99 percent / HCl; methanol / 16 h / 25 °C 4.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 4.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 5.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 6.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 7.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 8.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme