Total synthesis of Coronofacic Acid (Charette):
| Reference: | Moreau, B.; Ginisty, M; Alberico, D.; Charette, A. B. J. Org. Chem. 2006, 72, 1235. DOI |
| Reactions: | O-C(O)R → O-H • CompE+-CarboxEster/CarboxEster+H2O • CarboxEster → CarboxAcid • Aldol-BR2 → Aldol • CarboxEster enolate+Aldehyde • Diels-Alder, Intram, Ene • Cyclopentanone • Bicyclo(430) • Dehydration → Enoate • Ketone epimerization • Stereoconvergent • Allyl-OH → Enone • CarboxEster → EnolBorane • |
| Reagents: | B(OTf)Bu2 • NEtiPr2 • PPh3, DEAD • CuCl • TsOH • CrO3Cl·PyH (PCC) • DMSO (solvent) • HCl, THF • |