1.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 2.1: KOH / H2O; methanol / 2 h / 60 °C 3.1: 1.5 g / TsOH / CH2Cl2 / 1 h / 20 °C 4.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C 5.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 6.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 7.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 8.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 9.1: 81 percent / pyridine / 3 h / Heating 10.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 11.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 12.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 13.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 14.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 15.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 16.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 16.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 17.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 18.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1.1: 75 percent / PPh₃ / CH₂Cl₂ / 0.17 h / 0 &deg;C<br />2.1: tetrahydrofuran / 2.5 h / -78 - 0 &deg;C<br />2.2: 70 percent / HMPA / tetrahydrofuran / -78 - 20 &deg;C<br />3.1: 74 percent / AcOH / H₂O / 16 h / 100 &deg;C<br />4.1: 78 percent / tetrahydrofuran / -20 &deg;C<br />5.1: 88 percent / propionic acid / 2 h / Heating<br /> <br /> &nbsp;