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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: Alkene -> Diol-1,2 • O-H -> O-SO2R • O-H -> O-SiMe3 • Aldehyde -> Alkyl-OH • O-H -> O-SO2R • Ketone enolate+Alkyl-X • Ketone enolate+Alkyl-X, Intram • Grob fragmentation • Friedel-Crafts Acylation, Ene • Nitrile -> Aldehyde • CarboxAmide -> Nitrile • Alkyl-OTs -> Alkyl-H •
Reagents: Acetic anhydride, trifluoro • OsO4 • NMe3(O) • MeSO2Cl, NEt3 • SiMe3-Cl • LiNiPr2 • KOtAm • NaNH2 • TsCl • AlHiBu2 • AlHiBu2 • TsCl • BHEt3-Li+ • DMAP •

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