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Total synthesis of Bergamotene, α-trans:
Reference: Larson, S. D.; Monti, S. A. J. Am. Chem. Soc. 1977, 99, 8015. DOI
Keywords: O-H → O-SiMe3 • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Ketone enolate+Alkyl-X (intram) • Baldwin rules • Alkyl-X+Enolate (intram) • Cyclobutane • Friedel-Crafts Acylation, Ene • Cyclopentanone • Bicyclo(321) • Nitrile → Aldehyde • CompRed-Nitrile/Alkene+M-H • CarboxAmide → Nitrile • Alkyl-X → Alkyl-H • Aldehyde → CH3 • Grob fragmentation • Alkene → Diol-1,2 • O-H → O-SO2R • Aldehyde → Alkyl-OH • O-H → O-SO2R •
Reagents: Acetic anhydride, trifluoro • OsO4 • NMe3(O) • Sulfonyl chloride, methane, NEt3 • SiMe3-Cl • LiNiPr2 • KOtAm • TsCl, Py • AlHiBu2 • AlHiBu2 • TsCl • BH(Et)3-Li+ • DMAP • NaNH2

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