1: 1.) BuLi, HMPA / 1.) THF, 0 deg C, 2.) THF, RT, 9 h 2: 1.) (COCl)2, DMSO, 2.) Et3N 3: 100 percent / BuLi / tetrahydrofuran / -78 - 0 °C 4: 75 percent / toluene / 36 h / 200 °C 5: 80 percent / 1 N aq. HCl / tetrahydrofuran; acetone 6: 72 percent / NaBH4, CeCl3 / ethanol 7: 74 percent / diethyl azodicarboxylate, Ph3P, BzONa / tetrahydrofuran 8: 81 percent / (MeO)3BF4 9: 79 percent / ethanol. NaOEt 10: 99 percent / imidazole / dimethylformamide 11: 75 percent / tetrahydrofuran / Ambient temperature 12: 89 percent / tetrabutylammonium fluoride / diethyl ether / Ambient temperature 13: 1.) Bu3SnH, AIBN, 2.) SiO2 / 1.) benzene 14: 90 percent / m-CPBA, NaHCO3 15: 70 percent / BF3*Et2O / -78 - 20 °C 16: NH2OH*HCl, NaOAc / ethanol 17: carbonyldiimidazole / CH2Cl2 / Ambient temperature 18: 1.) LiNEt2, 2.) 2,6-di-tert-butyl-4-methylphenol / 1.) THF, 0 deg C, 30 min, 2.) THF, 30 min 19: 2.) H2O / 1.) THF, -78 deg C 20: 96 percent / H2 / 10percent Pd/C / ethanol 21: 74 percent / Et3N / benzene 22: 97 percent / TsOH / methanol / 24 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4047608', constants.ctx, '0')">sodium tris(acetoxy)borohydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '969212', constants.ctx, '0')">benzene</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 95 percent / Et₃N / dimethylformamide<br />2: 1.) O₃, 2.) Me₂S, 3.) NaBH₄ <br />3: aq. NaIO₄ / CH₂Cl₂ / 0 &deg;C<br />4: 67 percent / NaBH(OAc)3 / benzene<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) O₃, 2.) Me₂S, 3.) NaBH₄ <br />2: aq. NaIO₄ / CH₂Cl₂ / 0 &deg;C<br />3: 67 percent / NaBH(OAc)3 / benzene<br /> <br /> &nbsp;