Total synthesis of Thujopsene (Dauben):
| Reference: | Dauben, W. G.; Ashcraft, A. C J. Am. Chem. Soc. 1963, 85, 3673. DOI |
| Reactions: | Enone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • Wolff-Kishner • Ketone → CH2 • Allylic oxidation → Enone • Enone → Allyl-OH • Jones oxidation • Alkyl-OH → Ketone • Mg-Alkyl+Ketone • Ketone+Mg-Alkyl • Dehydration → Ene • Simmons-Smith • Cyclopropane • Bicyclo(410) • |
| Reagents: | MeI • KOtBu • Hydrazine • Hydroxide, potassium • CrO4Na2 • Acetic anhydride • AlH4-Li+ • CH2I2, Zn/Cu • CrO3, H2SO4 (Jones) • Me-MgBr • Chloride, ammonium • |