1: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 2: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

<b>Multi-step reaction with 9 steps<br /> </b>1: 99.6 percent / Et₃N / dioxane / 14 h / 50 &deg;C<br />2: 245 mg / 2M LiBH₄ / tetrahydrofuran; diethyl ether / 15 h / Ambient temperature<br />3: 99 percent / DMAP, pyridine / 20 h / Ambient temperature<br />4: 134 mg / Ac₂O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h<br />5: 94 percent / pyridine / 18 h / Ambient temperature<br />6: 90 mg / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile; H₂O / 5 h / Ambient temperature<br />7: 61 percent / 2-methyl-propan-2-ol; CH₂Cl₂ / 1 h / 50 &deg;C<br />8: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature<br />9: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C then 0 deg C, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 61 percent / 2-methyl-propan-2-ol; CH₂Cl₂ / 1 h / 50 &deg;C<br />2: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature<br />3: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C then 0 deg C, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature<br />2: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C then 0 deg C, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 94 percent / pyridine / 18 h / Ambient temperature<br />2: 90 mg / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile; H₂O / 5 h / Ambient temperature<br />3: 61 percent / 2-methyl-propan-2-ol; CH₂Cl₂ / 1 h / 50 &deg;C<br />4: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature<br />5: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C then 0 deg C, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 90 mg / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile; H₂O / 5 h / Ambient temperature<br />2: 61 percent / 2-methyl-propan-2-ol; CH₂Cl₂ / 1 h / 50 &deg;C<br />3: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature<br />4: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C then 0 deg C, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 134 mg / Ac₂O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h<br />2: 94 percent / pyridine / 18 h / Ambient temperature<br />3: 90 mg / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile; H₂O / 5 h / Ambient temperature<br />4: 61 percent / 2-methyl-propan-2-ol; CH₂Cl₂ / 1 h / 50 &deg;C<br />5: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature<br />6: 94 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C then 0 deg C, 2 h<br /> <br /> &nbsp;