1: 50percent aq. AcOH / 72 h / Ambient temperature View Scheme

1: 50percent aq. AcOH / 72 h / Ambient temperature View Scheme

<b>Multi-step reaction with 13 steps<br /> </b>1: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C<br />2: 82 percent / xylene / 18 h / Heating<br />3: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 &deg;C<br />4: 86 percent / NaBH₄ / ethanol<br />5: 93 percent / imidazole / dimethylformamide<br />6: 94 percent / xylene / 7 h / Heating<br />7: 81 percent / tetrahydrofuran / -78 &deg;C<br />8: 85 percent / N-Methylmorpholine-N-oxide, OsO₄ <br />9: 93 percent / anhydr. CuSO₄, TsOH<br />10: 75 percent / tetrahydrofuran / 24 h / Ambient temperature<br />11: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />12: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />13: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 81 percent / tetrahydrofuran / -78 &deg;C<br />2: 85 percent / N-Methylmorpholine-N-oxide, OsO₄ <br />3: 93 percent / anhydr. CuSO₄, TsOH<br />4: 75 percent / tetrahydrofuran / 24 h / Ambient temperature<br />5: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />6: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />7: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />2: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />3: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: 86 percent / NaBH₄ / ethanol<br />2: 93 percent / imidazole / dimethylformamide<br />3: 94 percent / xylene / 7 h / Heating<br />4: 81 percent / tetrahydrofuran / -78 &deg;C<br />5: 85 percent / N-Methylmorpholine-N-oxide, OsO₄ <br />6: 93 percent / anhydr. CuSO₄, TsOH<br />7: 75 percent / tetrahydrofuran / 24 h / Ambient temperature<br />8: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />9: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />10: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 15 steps<br /> </b>1: HBr, Ac₂O<br />2: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH<br />3: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C<br />4: 82 percent / xylene / 18 h / Heating<br />5: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 &deg;C<br />6: 86 percent / NaBH₄ / ethanol<br />7: 93 percent / imidazole / dimethylformamide<br />8: 94 percent / xylene / 7 h / Heating<br />9: 81 percent / tetrahydrofuran / -78 &deg;C<br />10: 85 percent / N-Methylmorpholine-N-oxide, OsO₄ <br />11: 93 percent / anhydr. CuSO₄, TsOH<br />12: 75 percent / tetrahydrofuran / 24 h / Ambient temperature<br />13: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />14: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />15: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1: 93 percent / imidazole / dimethylformamide<br />2: 94 percent / xylene / 7 h / Heating<br />3: 81 percent / tetrahydrofuran / -78 &deg;C<br />4: 85 percent / N-Methylmorpholine-N-oxide, OsO₄ <br />5: 93 percent / anhydr. CuSO₄, TsOH<br />6: 75 percent / tetrahydrofuran / 24 h / Ambient temperature<br />7: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />8: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />9: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 94 percent / xylene / 7 h / Heating<br />2: 81 percent / tetrahydrofuran / -78 &deg;C<br />3: 85 percent / N-Methylmorpholine-N-oxide, OsO₄ <br />4: 93 percent / anhydr. CuSO₄, TsOH<br />5: 75 percent / tetrahydrofuran / 24 h / Ambient temperature<br />6: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />7: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />8: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 12 steps<br /> </b>1: 82 percent / xylene / 18 h / Heating<br />2: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 &deg;C<br />3: 86 percent / NaBH₄ / ethanol<br />4: 93 percent / imidazole / dimethylformamide<br />5: 94 percent / xylene / 7 h / Heating<br />6: 81 percent / tetrahydrofuran / -78 &deg;C<br />7: 85 percent / N-Methylmorpholine-N-oxide, OsO₄ <br />8: 93 percent / anhydr. CuSO₄, TsOH<br />9: 75 percent / tetrahydrofuran / 24 h / Ambient temperature<br />10: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature<br />11: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature<br />12: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.<br /> <br /> &nbsp;