1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 2: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 3: 97 percent / NaOAc / 17 h / 20 °C 4: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 5: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 6: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme

<b>Multi-step reaction with 7 steps<br /> </b>1.1: ethanol / 25 &deg;C<br />1.2: 64 percent / N₂H₄*H₂O / ethanol / 5 h / Heating<br />2.1: 61 percent / EDCI; DMAP / CH₂Cl₂ / 19 h / 25 &deg;C<br />3.1: 67 percent / p-toluenesulfonyl chloride; Et₃N / CH₂Cl₂ / 20 h / 25 &deg;C<br />4.1: 96 percent / EDCI; DMAP / CH₂Cl₂ / 16 h / 0 - 25 &deg;C<br />5.1: 53 percent / various solvent(s) / 90 h / 230 &deg;C<br />6.1: Chiracel OD / propan-2-ol; hexane<br />7.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 &deg;C<br />7.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: 79 percent / AcOH / tetrahydrofuran / 35 &deg;C<br />2.1: 67 percent / p-toluenesulfonyl chloride; Et₃N / CH₂Cl₂ / 20 h / 25 &deg;C<br />3.1: 96 percent / EDCI; DMAP / CH₂Cl₂ / 16 h / 0 - 25 &deg;C<br />4.1: 53 percent / various solvent(s) / 90 h / 230 &deg;C<br />5.1: Chiracel OD / propan-2-ol; hexane<br />6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 &deg;C<br />6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: 61 percent / EDCI; DMAP / CH₂Cl₂ / 19 h / 25 &deg;C<br />2.1: 67 percent / p-toluenesulfonyl chloride; Et₃N / CH₂Cl₂ / 20 h / 25 &deg;C<br />3.1: 96 percent / EDCI; DMAP / CH₂Cl₂ / 16 h / 0 - 25 &deg;C<br />4.1: 53 percent / various solvent(s) / 90 h / 230 &deg;C<br />5.1: Chiracel OD / propan-2-ol; hexane<br />6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 &deg;C<br />6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 &deg;C<br /> <br /> &nbsp;