1: 95 percent / 1M LiOH / H2O; dioxane / 2 h / 10 °C 2: thioanisole, BrSiMe3, CF3COOH / 1 h / 0 °C View Scheme

<b>Multi-step reaction with 15 steps<br /> </b>2: 90 percent / LiOH*H₂O / dioxane; H₂O / 1) RT, 5 h, ultrasound, 2) 50 deg C, 15 h<br />3: 1-chloro-1-(N,N-dimethylamino)-2-methyl-1-propene / CH₂Cl₂ / 0.25 h / 0 &deg;C<br />4: 1) n-BuLi / 1) THF, hexane, -70 deg C, 20 min, 2a) -70 deg C to RT, 2b) RT, 15 h<br />5: H₂ / &lt;(R)-(RuCl(p-cymene)BINAP&gt;Cl / methanol; CH₂Cl₂ / 72 h / 50 &deg;C / 37503 Torr<br />6: 97 percent / aq. HOAc / 3 h / 50 &deg;C<br />7: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h<br />8: 85 percent / H₂ / (R,R)-&lt;Rh(1,5-COD)(DIPAMP)&gt;BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature<br />9: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature<br />10: hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 15 h / -10 deg C to RT<br />11: 71 percent / HOAc / H₂O / 4 h / 50 &deg;C<br />12: 96 percent / Bu₄NF*3H₂O / dimethylformamide / 2 h / Ambient temperature<br />13: EDCI / CH₂Cl₂ / 15 h / -10 deg C to RT<br />14: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature<br />15: aq. KHCO₃ / CHCl₃ / 1) RT, 2 h, 2) 50 deg C, 30 min<br /> <br /> &nbsp;

<b>Multi-step reaction with 13 steps<br /> </b>1: 90 percent / DMAP / CH₂Cl₂ / 0.17 h<br />2: 30percent H₂O₂, HCO₂H / CH₂Cl₂ / 0.5 h / 0 &deg;C<br />3: 2) 2M Na₂CO₃ / 1) Pd(PPh₃)4 / 1) THF, 1 h, reflux, 2) 24 h, reflux<br />4: 80 percent / Cs₂CO₃ / methanol / 2 h / Ambient temperature<br />5: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h<br />6: 85 percent / H₂ / (R,R)-&lt;Rh(1,5-COD)(DIPAMP)&gt;BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature<br />7: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature<br />8: hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 15 h / -10 deg C to RT<br />9: 71 percent / HOAc / H₂O / 4 h / 50 &deg;C<br />10: 96 percent / Bu₄NF*3H₂O / dimethylformamide / 2 h / Ambient temperature<br />11: EDCI / CH₂Cl₂ / 15 h / -10 deg C to RT<br />12: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature<br />13: aq. KHCO₃ / CHCl₃ / 1) RT, 2 h, 2) 50 deg C, 30 min<br /> <br /> &nbsp;

<b>Multi-step reaction with 13 steps<br /> </b>1: 91 percent / 1M aq. NaOH / dioxane / 15 h / Ambient temperature<br />2: 1) n-BuLi / 1) THF, hexane, -70 deg C, 20 min, 2a) -70 deg C to RT, 2b) RT, 15 h<br />3: H₂ / &lt;(R)-(RuCl(p-cymene)BINAP&gt;Cl / methanol; CH₂Cl₂ / 72 h / 50 &deg;C / 37503 Torr<br />4: 97 percent / aq. HOAc / 3 h / 50 &deg;C<br />5: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h<br />6: 85 percent / H₂ / (R,R)-&lt;Rh(1,5-COD)(DIPAMP)&gt;BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature<br />7: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature<br />8: hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 15 h / -10 deg C to RT<br />9: 71 percent / HOAc / H₂O / 4 h / 50 &deg;C<br />10: 96 percent / Bu₄NF*3H₂O / dimethylformamide / 2 h / Ambient temperature<br />11: EDCI / CH₂Cl₂ / 15 h / -10 deg C to RT<br />12: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature<br />13: aq. KHCO₃ / CHCl₃ / 1) RT, 2 h, 2) 50 deg C, 30 min<br /> <br /> &nbsp;