hydrogen; platinum in 1,4-dioxane Catalytic hydrogenation; P=2280 Torr; 8 h;

palladium on activated charcoal; 2-methoxy-ethanol; triethylamine Hydrogenation;

1.1: 80 percent / LDA / tetrahydrofuran / 0.25 h / -40 °C 2.1: 90 percent / SOCl2; TEA / CH2Cl2 / 0.17 h / -30 °C 3.1: BBr3 / CH2Cl2 / 0.25 h / -78 °C 4.1: H2; TEA / Pd-black / dioxane; H2O / 1 h 5.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h 6.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 7.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 8.1: Zn / acetic acid / 0.03 h 9.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 9.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 10.1: NH2OH*HCl; TEA / methanol / 0.5 h 11.1: CDI / tetrahydrofuran / 0.75 h 12.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 13.1: 80 percent / formic acid / 1 h / 80 °C 14.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 15.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 16.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 2: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 2: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 3: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

1: 80 percent / formic acid / 1 h / 80 °C 2: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 3: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 4: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

1.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 2.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 3.1: Zn / acetic acid / 0.03 h 4.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 4.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 5.1: NH2OH*HCl; TEA / methanol / 0.5 h 6.1: CDI / tetrahydrofuran / 0.75 h 7.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 8.1: 80 percent / formic acid / 1 h / 80 °C 9.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 10.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 11.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

1.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 1.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 2.1: NH2OH*HCl; TEA / methanol / 0.5 h 3.1: CDI / tetrahydrofuran / 0.75 h 4.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 5.1: 80 percent / formic acid / 1 h / 80 °C 6.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 7.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 8.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

1: NH2OH*HCl; TEA / methanol / 0.5 h 2: CDI / tetrahydrofuran / 0.75 h 3: 68 percent / polyposphoric acid / 0.75 h / 100 °C 4: 80 percent / formic acid / 1 h / 80 °C 5: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 6: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 7: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

1.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h 2.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 3.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 4.1: Zn / acetic acid / 0.03 h 5.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 5.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 6.1: NH2OH*HCl; TEA / methanol / 0.5 h 7.1: CDI / tetrahydrofuran / 0.75 h 8.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 9.1: 80 percent / formic acid / 1 h / 80 °C 10.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 11.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 12.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme