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Total synthesis of Hirsutene:
Reference: Ley, S. V.; Murray, P.J. Chem. Commun. 1982, 1252. DOI
Keywords: Ketone → Ketone-α-SeR • CarboxEster → Alkyl-OH • Selenoxide-Ei → KetoEsterEnone • Ketoester → Enone • CarboxEster → CarboxEster-α-SeR • Mitsunobu → SeR • Alkyl-OH → Alkyl-SeR • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd Cu-R • Hydrogenolysis C-Se • Alkyl-SeR → Alkyl-H • Ketone protection enolate • Hydrogenolysis C-Se • Alkyl-SeR → Alkyl-H • Mechanism • Alkyl-OH → Alkyl-SeR • Cationic cyclization •
Reagents: Alkyl-MgX • Mg° • NaH • SePh-Cl • H2O2 • RaNi • LiNiPr2 • AlH4-Li+ • SePh-Phthalimide • PBu3 • RaNi • PPh3=CH2 • CuBr·SMe2 • DMSO (solvent) • SePh-Phthalimide • SnCl4

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