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Total synthesis of Pentalenene:
Reference: Paquette, L. A.; Geng, F. Org. Lett. 2002, 4, 4547 DOI
Keywords: O-H → O-C(O)R • Ketone → Alkyl-OH • O-H → O-C(O)R • Aldol-Li → Aldol • Ketone enolate+Ketone • Ketone enolate+Me-I • Alkyl-OAc → Alkyl-H • 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 •
Reagents: DMAP • Li°/NH3 • Li°/NH3 • KOtBu • MeI • Li°/NH3 • DMAP • Na° • HMPA (solvent) • Vinyl-Li • Alkynyl-Li •

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