1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 6: 97 percent / TBAF / tetrahydrofuran / 0.33 h 7: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 8: 98 percent / DBU / xylene / 16.5 h / Heating 9: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme

1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 5: 100 percent / 4-DMAP, pyridine / 36 h 6: 98 percent / NaBH4 / methanol / 2.5 h 7: 94 percent / DIEA / CH2Cl2 / 6 h 8: 100 percent / TBAF / tetrahydrofuran / 24 h 9: 69 percent / 4-DMAP / acetonitrile / 11.5 h 10: 0.25 h / 24 - 200 °C / 12 Torr 11: DIEA / methanol / 2 h 12: 93 percent / 2 N aq. HCl / methanol / 23 h / Heating 13: 100 percent / DIEA / methanol / 4 h View Scheme

1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 6: 97 percent / TBAF / tetrahydrofuran / 0.33 h 7: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 8: 98 percent / DBU / xylene / 16.5 h / Heating 9: CAN / acetonitrile; H2O / 0.28 h / 0 °C 10: DMAP, pyridine / 22 h View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 97 percent / NaH, TBAI / tetrahydrofuran / 1.) r.t., 5 min, 2.) 24 h<br />2: 99 percent / LiAlH₄ / tetrahydrofuran / 0.67 h<br />4: 96 percent / H₂ / 10percent Pd/C / tetrahydrofuran; methanol / 26 h<br />5: 92 percent / imidazole / dimethylformamide / 15 h<br />6: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: imidazole / dimethylformamide / 15 h<br />2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h<br /> <br /> &nbsp;