image

Total synthesis of Silphinene:
Reference: Crimmmins, M. T.; Mascarella, S. W. J. Am. Chem. Soc. 1986, 108, 3435 DOI
Keywords: Enolether -> Ketone • Krapcho Decarboxylation • Saegusa oxidation • Ketone -> Enolphosphate • Vinyl-OP(O)(OR)2 -> Vinyl-H • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd-Alkylation • Aldol-Na -> KetoEsterEnone • Cu-Me+Enone • Ketone -> Enolsilane • Alkyl-X -> Alkyl-H • Radical reduction(C-I) • Cyclobutane opening •
Reagents: CuI·PBu3 • HClO4 • NaOMe • LiCuMe2 • Chloride, lithium • Fluoride, Bu4N+ • Pd(OAc)2 • Quinone • SiMe3-I • Acetonitrile (solvent) • HSnBu3 • LiNiPr2 • P(O)(OR)2Cl • NHMe2

Syntheses Home