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Total synthesis of (+)-Longifolene:
Reference: Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609
Keywords: Alkyl-OH -> Aldehyde • O-H -> O-C(S)OR • CarboxEster -> Alkyl-OH • O-H -> O-C(O)R • Alkyl-OMe -> Alkyl-I • Aldol-Li -> Aldol • CarboxEster enolate+Aldehyde • Lactone-6 • Cyclopropane alkylation • Diels-Alder, Intram • Hydrogenation Alkene • Radical reduction(C-OR) • Alkyl-OH -> Alkyl-H(2°) • Barton-McCombie reduction • Radical reduction(C-I) • Alkyl-X -> Alkyl-H(2°) • Ester Pyrolysis • Cyclopentadienide+Ketone • Mechanism • Resolution • ConjAdd-Alkylation • Cyclopropane • Fulvene+Li-R •
Reagents: Pyrrolidine • MnO2 • LiNiPr2 • CdCl2 • Cyclopentadiene • BF3·OEt2 • S=C(OPh)Cl • HSnBu3 • H2, Pd • AlH4-Li+ • Acetic anhydride • Iodide, sodium • SiMe3-Cl • HSnBu3 • Flash vacuum pyrolysis • MeLi •

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