Total synthesis of Isolongifolene (Piers):
| Reference: | Piers, E.; Zbozny, M. Can. J. Chem., 1979, 57, 2249. DOI |
| Reactions: | Allylic oxidation → Enone • Decarboxylation Krapcho • Ketone → Enone • Enone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • Hydroboration → Alkyl-OH • CompRed-Alkene/Ester+M-H • Enone enolate+Alkyl-X • Alkyl-X+Enolate (intram) • Bicyclo(221) • Cyclopentane • ConjAdd Cu-Me • Cu-Me+Enone • ConjAdd Cu-Me • Cu-Me+Enone • Ketone-α-Halo → Enone • Enone → Dienone • Ketal → Ketone • Wittig-methyl • CompE+-Ketone/CarboxEster+Wittig • O-H → O-C(O)R • Enone → Ketal • O-C(O)R → O-H • O-H → O-SO2Ar • Ketone → Ketone-α-Halo • |
| Reagents: | Photochemistry • NBS • Carbonate, calcium • KOtBu • PPh3=CH2 • BH(Siam)2 • H2O2, NaOH • Bromide, lithium • Glycol • AlH4-Li+ • TsCl, Py • KOtBu • DDQ • Me-Cuprate • Tribromide • Carbonate, lithium • Me-Cuprate • Acetic anhydride, Py • HMPA (solvent) • |