Total synthesis of Copaene:
| Reference: | Heathcock, C. J. Am. Chem. Soc. 1966, 88, 4112-4113. DOI |
| Reactions: | O-H → O-SO2Ar • Epoxidation, peracid • Epoxide+M-OR • 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 • TsCl, Py • H2SO4 • DMSO (solvent) • HBr • Acetic acid • Alkyl-Li • CrO3, H2SO4 (Jones) • POCl3 • Me-Li • H2, Pd • POCl3 • Wieland-Miescher • Perbenzoic acid, 3-chloro • |