Total synthesis of Bergamotene, α-trans:
| Reference: | Larson, S. D.; Monti, S. A. J. Am. Chem. Soc. 1977, 99, 8015. DOI |
| Reactions: | 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 • Bicyclo(311) • Alkene → Diol-1,2 • O-H → O-SO2Me • Aldehyde → Alkyl-OH • O-H → O-SO2Ar • |
| 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 • |