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Total synthesis of Longifolene:
Reference: Volkmann, R. A.; Andrews, G. C.; Johnson, W.S. J. Am. Chem. Soc. 1975, 97, 4777–4779. DOI
Keywords: Ketone enolate+Br2 • ConjAdd Cu-R • Cu-Alkyl+Enone • Enone+Cu-R • EnolAcetate → Enolate • Dehydrohalogenation → Enone • Enone → Allyl-OH • Cationic cyclization • Alkyl-OH → Alkyl-H(3°) • Alkene isomerization • Alkene cleavage • Ketone enolate+Me-I • Ketone+Li-Alkyl • Li-Me+Ketone • Dehydration → Ene • Mechanism •
Reagents: Acetyl chloride • AlH4-Li+ • ZnBr2 • Acetic acid, trifluoro • BH3CN-Na+ • TsOH • Periodate, sodium • RuO4 • LiNiPr2 • MeI • SOCl2

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