image

Total synthesis of (+)-Longifolene:
Reference: Lei, B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 4609 DOI
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 • Mechanism •
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 •

Syntheses Home