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Total synthesis of Silphinene:
Reference: Crimmins, M. T.; Mascarella, S. W. J. Am. Chem. Soc. 1986, 108, 3435 DOI
Keywords: EnolEther → Ketone • Krapcho Decarboxylation • Saegusa oxidation • Ketone → Enone • Ketone → Enolphosphate • EnolPhosphate → Vinyl-H • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd-Alkylation • ConjAdd Cu-R • Aldol-Na → KetoEsterEnone • Cu-Me+Enone • Ketone → EnolSilane • Alkyl-X → Alkyl-H • Radical reduction(C-I) • DeMayo cycloaddition • Photochemistry 2+2 • Cyclobutane opening •
Reagents: CuI·PBu3 • HClO4 • NaOMe • LiCuMe2 • Chloride, lithium • Fluoride, R4N+ • Pd(OAc)2 • Quinone • SiMe3-I • Acetonitrile (solvent) • HSnBu3 • LiNiPr2 • P(O)(OR)2Cl • NHMe2 • Photochemistry •

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