perchloric acid in tetrahydrofuran; dichloromethane

1: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, -78 deg C, 2.) toluene 2: HMPA / tetrahydrofuran / -78 - 20 °C 3: TBAF 4: 1.) LDA, HMPA / 1.) THF, -78 deg C 5: H2 / Lindlar catalyst 6: 48percent HBr / methanol 7: 96 percent / O2, NaHCO3 / methanol 8: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme

1: 1.) Na2S2O4, H2O, 2.) i-Pr2NEt / 1.) MeOH, THF, 2.) CH2Cl2 2: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, -78 deg C, 2.) toluene 3: HMPA / tetrahydrofuran / -78 - 20 °C 4: TBAF 5: 1.) LDA, HMPA / 1.) THF, -78 deg C 6: H2 / Lindlar catalyst 7: 48percent HBr / methanol 8: 96 percent / O2, NaHCO3 / methanol 9: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme

1: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, -78 deg C, 2.) toluene 2: HMPA / tetrahydrofuran / -78 - 20 °C 3: TBAF 4: 1.) LDA, HMPA / 1.) THF, -78 deg C 5: H2 / Lindlar catalyst 6: 48percent HBr / methanol 7: 96 percent / O2, NaHCO3 / methanol 8: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme

1: HMPA / tetrahydrofuran / -78 - 20 °C 2: TBAF 3: 1.) LDA, HMPA / 1.) THF, -78 deg C 4: H2 / Lindlar catalyst 5: 48percent HBr / methanol 6: 96 percent / O2, NaHCO3 / methanol 7: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme

1: 1.) LDA, HMPA / 1.) THF, -78 deg C 2: H2 / Lindlar catalyst 3: 48percent HBr / methanol 4: 96 percent / O2, NaHCO3 / methanol 5: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme

1: 1.) LDA, HMPA / 1.) THF, -78 deg C 2: H2 / Lindlar catalyst 3: 48percent HBr / methanol 4: 96 percent / O2, NaHCO3 / methanol 5: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme

1: TBAF 2: 1.) LDA, HMPA / 1.) THF, -78 deg C 3: H2 / Lindlar catalyst 4: 48percent HBr / methanol 5: 96 percent / O2, NaHCO3 / methanol 6: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme

1: 48percent HBr / methanol 2: 96 percent / O2, NaHCO3 / methanol 3: 47 percent / 70percent HClO4 / CH2Cl2; tetrahydrofuran View Scheme