1: ICl / CCl4; CH2Cl2 / 24 h / 0 - 20 °C 2: chlorotrimethylsilane; H2O; NaI / acetonitrile / 5 h / 65 °C 3: sodium hydride; LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 20 h / 70 °C 4: hexamethylditin / benzene / 1.5 h / Photolysis View Scheme

<b>Multi-step reaction with 10 steps<br /> </b>1.1: 78 percent / NaBH₄ / ethanol / 1 h / -40 &deg;C<br />2.1: i-Pr₂EtN / CH₂Cl₂ / 0 - 20 &deg;C<br />3.1: i-PrMgCl / tetrahydrofuran / 1 h / -40 &deg;C<br />3.2: CuCN*2LiCl / tetrahydrofuran / 0.25 h / -40 &deg;C<br />3.3: 69 percent / tetrahydrofuran / 1.25 h / -40 - 20 &deg;C<br />4.1: t-BuOK / tetrahydrofuran / 1 h / 0 &deg;C<br />4.2: 27 percent / tetrahydrofuran / 36 h / Heating<br />5.1: 96 percent / LAH / diethyl ether<br />6.1: t-BuOOH; Ti(O-i-Pr)4; L-(+)-diethyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂; decane / 2 h / -20 &deg;C<br />7.1: LAH / diethyl ether / 0 - 20 &deg;C<br />8.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 &deg;C<br />9.1: sodium chlorite; sodium dihydrogen phosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 16 h / 20 &deg;C<br />10.1: TFA / 16 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: i-PrMgCl / tetrahydrofuran / 1 h / -40 &deg;C<br />1.2: CuCN*2LiCl / tetrahydrofuran / 0.25 h / -40 &deg;C<br />1.3: 69 percent / tetrahydrofuran / 1.25 h / -40 - 20 &deg;C<br />2.1: t-BuOK / tetrahydrofuran / 1 h / 0 &deg;C<br />2.2: 27 percent / tetrahydrofuran / 36 h / Heating<br />3.1: 96 percent / LAH / diethyl ether<br />4.1: t-BuOOH; Ti(O-i-Pr)4; L-(+)-diethyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂; decane / 2 h / -20 &deg;C<br />5.1: LAH / diethyl ether / 0 - 20 &deg;C<br />6.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 &deg;C<br />7.1: sodium chlorite; sodium dihydrogen phosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 16 h / 20 &deg;C<br />8.1: TFA / 16 h / 20 &deg;C<br /> <br /> &nbsp;