Total synthesis of Clovene (Schultz):
| Reference: | Schultz, A. G.; Dittani, J. P. J. Org. Chem., 1983, 48, 2318. DOI |
| Reactions: | Enone enolate+Alkyl-X • Alkyl-X+Enolate • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Enone-β-OR → Enone • Enone-β-OR+Al-H • Stork-Danheiser • Enone enolate+Alkyl-X • Alkyl-X+Enolate (intram) • Cyclohexane • Bicyclo(331) • Enone enolate+Alkyl-X • Allyl-X+Enolate • ConjReduct Enone • Ozonolysis • Enone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • Aldol-K → Enone • Cyclopentenone • Bicyclo(430) • Enol → EnAmine • Claisen acylation, formate • Jones oxidation • Acetate pyrolysis • Ketone → Alkyl-OH • Enone enolate+Alkyl-X • |
| Reagents: | LiNiPr2 • MeI • LiNiPr2 • AlH4-Li+ • HCl, H2O • LiNiPr2 • LiNiPr2 • BH(sBu3)-K+ • O3; Me2S • Allyl-Br • HMPA (solvent) • Hydroxide, potassium • Li°/NH3 • KOtBu • O=C(OEt)Cl • AlH4-Li+ • Hydroxide, potassium • NaNH2 • Formate, ethyl • CrO3, H2SO4 (Jones) • |