Total synthesis of Pentalenene (Paquette):
| Reference: | Paquette, L. A.; Geng, F. Org. Lett. 2002, 4, 4547 DOI |
| Reactions: | Aldol-Li → Aldol • Ketone enolate+Ketone • Cyclopentane • Cyclopentenone • Bicyclo(330) • Ketone enolate+Me-I • Alkyl-OAc → Alkyl-H • Ketone → CH2 • Mechanism • ConjReduct Enone • ConjReduct-Elimination • Ketone-α-OR → Ketone • Electrocyclic-4π • Electrocyclic-8π • Li-Vinyl+Ketone • Enone+Li-R • Li-Alkynyl+Ketone • Enone+Li-R • Li/H → Li-Alkynyl • O-H → O-C(O)R • Ketone → Alkyl-OH • O-H → O-C(O)R • |
| Reagents: | Acetic anhydride, DMAP • Li°/NH3 • Li°/NH3 • KOtBu • MeI • Li°/NH3 • Acetic anhydride, DMAP • Na° • HMPA (solvent) • Vinyl-Li • Alkynyl-Li • |