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Total synthesis of Copaene:
Reference: Heathcock, C. J. Am. Chem. Soc. 1966, 88, 4112-4113. DOI
Keywords: O-H → O-SO2R • Epoxidation, peracid • Epoxide → Diol • Epoxide+O-R • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Cyclobutane • Bicyclo(311) • O-Bn → O-H • Li-Alkyl+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Li-Me+Ketone • Ketone+Li-Alkyl • Hydrogenation Alkene • Dehydration → Ene • Ketal → Ketone • Alkyl-OH → Ketone • Ketone → Ketal •
Reagents: Glycol • Perbenzoic acid, 3-chloro • TsCl, Py • H2SO4 • DMSO (solvent) • HBr • Acetic acid • LiCHMe2 • CrO3, H2SO4 (Jones) • POCl3 • MeLi • H2, Pd • POCl3 • Perbenzoic acid, 3-chloro • Wieland-Miescher •

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