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Total synthesis of Sesquifenchene:
Reference: Grieco, P. A., Masaki, Y. J. Org. Chem. 1975, 40, 150. DOI
Keywords: Alkyl-OH → CarboxAcid • Ketone → Ketal • CarboxEster → Alkyl-OH • O-H → O-SO2R • Ketal → Ketone • Prins • Cyclopropane • Cyclopropane opening • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Alkyl-X → Alkyl-H • Radical reduction(C-Br) • Alkyl-X → Alkyl-I • Alkyl-X → Alkyl-SO2R • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Alkyl-SO2R → Alkyl-H • Wittig-methyl •
Reagents: Formic acid • Formaldehyde • CrO3, H2SO4 (Jones) • HBr • Acetic acid • Glycol • LiNiPr2 • MeI • HSnBu3 • AIBN • AlH4-Li+ • TsCl, Py • Iodide, sodium • Sulfinate, benzene • DMF (solvent) • BuLi(n) • Allyl-Br • Li°/EtNH2 • Acetic acid • PPh3=CH2 • DMSO (solvent) •

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