1: (4-carboxy-n-butyl)-triphenylphosphonium bromide With potassium tert-butylate in tetrahydrofuran T=0°C; Wittig Olefination; 0.666667 h; Schlenk techniqueInert atmosphere; 2: (3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxy-1-octenyl]perhydrocyclopenta[b]furan-2,5-diol in tetrahydrofuran T=20°C; Wittig Olefination; 1 h; Schlenk techniqueInert atmosphere;

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Yield given;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1.) imidazole, 2.) potassium cyanide / 1.) methylene chloride, room temp., 2.) ethanol, room temp.<br />2: 96 percent / N-iodosuccinimide / CH₂Cl₂ / -20 &deg;C<br />3: 71 percent / tributyltin chloride, sodium cyanoborohydride, AIBN / 2-methyl-propan-2-ol / 5 h / Heating<br />4: 84 percent / DIBAl-H / toluene / -20 &deg;C<br />5: 93 percent / lithium chloride, (i-Pr)2NEt / acetonitrile / Ambient temperature<br />6: 89 percent / (S)-BINAl-H / tetrahydrofuran / -100 &deg;C<br />7: 98 percent / 1.5percent aqueous hydrochloric acid / tetrahydrofuran / Ambient temperature<br /> <br /> &nbsp;