1: 92 percent / NaBH4 / methanol / -78 - 25 °C 2: 82 percent / H2 / 10percent Pd/C, 70percent HClO4 / methanol / 25 °C / 2068.6 Torr 3: 2.) DIBAL / 1. 90 gradC, 50 h; 2. THF, 0 gradC, 1 h. View Scheme

<b>Multi-step reaction with 16 steps<br /> </b>1: 1.) Mg / 2.) THF, 0deg C, 1.5 h<br />2: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 &deg;C<br />3: pentane / 25 &deg;C / Irradiation<br />4: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 &deg;C<br />5: 94 percent / NaBH₄ / methanol / 0.25 h / 25 &deg;C<br />6: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 &deg;C<br />7: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 &deg;C / 760 Torr<br />8: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 &deg;C<br />10: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 &deg;C<br />11: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC<br />12: 97 percent / imidazole / dimethylformamide / 5 h / 25 &deg;C<br />13: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.<br />14: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 &deg;C<br />15: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.<br />16: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.<br /> <br /> &nbsp;

<b>Multi-step reaction with 15 steps<br /> </b>1: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 &deg;C<br />2: pentane / 25 &deg;C / Irradiation<br />3: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 &deg;C<br />4: 94 percent / NaBH₄ / methanol / 0.25 h / 25 &deg;C<br />5: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 &deg;C<br />6: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 &deg;C / 760 Torr<br />7: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 &deg;C<br />9: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 &deg;C<br />10: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC<br />11: 97 percent / imidazole / dimethylformamide / 5 h / 25 &deg;C<br />12: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.<br />13: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 &deg;C<br />14: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.<br />15: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.<br /> <br /> &nbsp;

<b>Multi-step reaction with 14 steps<br /> </b>1: pentane / 25 &deg;C / Irradiation<br />2: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 &deg;C<br />3: 94 percent / NaBH₄ / methanol / 0.25 h / 25 &deg;C<br />4: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 &deg;C<br />5: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 &deg;C / 760 Torr<br />6: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 &deg;C<br />8: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 &deg;C<br />9: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC<br />10: 97 percent / imidazole / dimethylformamide / 5 h / 25 &deg;C<br />11: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.<br />12: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 &deg;C<br />13: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.<br />14: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 &deg;C / 760 Torr<br />2: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 &deg;C<br />4: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 &deg;C<br />5: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC<br />6: 97 percent / imidazole / dimethylformamide / 5 h / 25 &deg;C<br />7: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.<br />8: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 &deg;C<br />9: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.<br />10: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.<br /> <br /> &nbsp;

<b>Multi-step reaction with 12 steps<br /> </b>1: 94 percent / NaBH₄ / methanol / 0.25 h / 25 &deg;C<br />2: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 &deg;C<br />3: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 &deg;C / 760 Torr<br />4: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 &deg;C<br />6: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 &deg;C<br />7: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC<br />8: 97 percent / imidazole / dimethylformamide / 5 h / 25 &deg;C<br />9: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.<br />10: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 &deg;C<br />11: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.<br />12: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.<br /> <br /> &nbsp;

<b>Multi-step reaction with 17 steps<br /> </b>1: 54 percent / PCC / CH₂Cl₂ / 2 h / 0 - 25 &deg;C<br />2: 1.) Mg / 2.) THF, 0deg C, 1.5 h<br />3: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 &deg;C<br />4: pentane / 25 &deg;C / Irradiation<br />5: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 &deg;C<br />6: 94 percent / NaBH₄ / methanol / 0.25 h / 25 &deg;C<br />7: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 &deg;C<br />8: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 &deg;C / 760 Torr<br />9: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 &deg;C<br />11: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 &deg;C<br />12: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC<br />13: 97 percent / imidazole / dimethylformamide / 5 h / 25 &deg;C<br />14: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.<br />15: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 &deg;C<br />16: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.<br />17: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.<br /> <br /> &nbsp;