1: Et3N / CH2Cl2 / Heating 2: TsOH / methanol / 20 °C 3: imidazole / dimethylformamide; CH2Cl2 / -60 °C 4: 91 percent / OsO4, NMO, H2O / acetone / 0 °C 5: 92 percent / TsOH / 20 °C 6: DMAP, Et3N / CH2Cl2 / 20 °C 7: Bu4NF / tetrahydrofuran / 20 °C 8: NaOH, H2O 9: 76 percent / cyclohexene / 5percent Pd/C / ethanol / Heating 10: 96 percent / HCl, H2O / methanol View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: DBU / acetonitrile / 0 &deg;C<br />2: 1.) methyl 2,2,2-trichloroacetimidate, Et₃N, 2.) PPTS / 1.) MeCN, -20 to -15 deg C, 2.) MeOH, H₂O, 20 deg C<br />3: 84 percent / H₂O₂ / H₂O; tetrahydrofuran / 0 - 20 &deg;C<br />4: 92 percent / Bu₄NF / tetrahydrofuran / -5 - 0 &deg;C<br />5: 88 percent / DIAD, PPh₃ / tetrahydrofuran / 0 &deg;C<br />6: 90 percent / tetrahydrofuran / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 86 percent / PPTS / methanol / 0 &deg;C<br />2: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -60 &deg;C<br />3: DBU / acetonitrile / 0 &deg;C<br />4: 1.) methyl 2,2,2-trichloroacetimidate, Et₃N, 2.) PPTS / 1.) MeCN, -20 to -15 deg C, 2.) MeOH, H₂O, 20 deg C<br />5: 84 percent / H₂O₂ / H₂O; tetrahydrofuran / 0 - 20 &deg;C<br />6: 92 percent / Bu₄NF / tetrahydrofuran / -5 - 0 &deg;C<br />7: 88 percent / DIAD, PPh₃ / tetrahydrofuran / 0 &deg;C<br />8: 90 percent / tetrahydrofuran / 20 &deg;C<br /> <br /> &nbsp;