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Total synthesis of Oleocanthal:
Reference: Smith, A. B.; Han, Q.; Breslin, P. A. S.; Beauchamp. G. K. Org. Let. 2005, 7, 5075. DOI
Reactions: Wittig-alkyl+Ketone • CompE+-Ketone/CarboxEster+Wittig • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Li-R → Zn-R • Mitsunobu → OC(O)R • Alkyl-OH → Alkyl-OC(O)R • CompNu-Alkyl-OH/Phenol+RC(O)X • Reductive elimination - X/OR • Mg-Vinyl+Aldehyde • RCM → Enone • Cyclopentenone • Diol-1,2 → Ketal • Enone → Ketone • CarboxEster → CarboxAcid • Ketal → Diol-1,2 • Diol-1,2 cleavage • Allyl-OH → Enone •
Reagents: Ribose • Acetone (react) • HCl, MeOH • PPh3, I2 • Zn° • Vinyl-MgX • Grubbs I • CrO3Cl·PyH (PCC) • H2, Pd • LiN(SiMe3)2 • ZnMe2 • Bromoacetate • PPh3=CH-Me • Hydroxide, lithium • PPh3, DEAD • Acetonitrile (solvent) • Periodate, sodium • LiNiPr2 • Imidazole • HMPA (solvent) • HMPA (solvent) • HOMe (react) •

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