Total synthesis of Capnellene (Paquette):
| Reference: | Paquette, L. A.; Stevens, K. E. Can. J. Chem. 1984, 62, 2415. DOI |
| Reactions: | Mg-Vinyl+Aldehyde • Enal+Mg-R • ConjAdd Cu-Me • Li-Alkynyl+Ketone • Li/H → Li-Alkynyl • Rupe • Propargyl-OH → Enone • Nazarov • Cyclopentenone • Bicyclo(330) • Allyl-OH → Enone • Ozonolysis • Cu-Vinyl+Enone • ConjAdd Cu-Vinyl • Mg-R → Cu-R • Aldol-K → Enone • Cyclopentenone • Bicyclo(330) • Hydrogenation Enone • Wittig-methyl • |
| Reagents: | Me-Cuprate • Alkynyl-Li • Formic acid • H2SO4 • Vinyl-MgX • MnO2 • P2O5 • Sulfonic acid, methane • Vinyl-MgX • CuI • O3; Me2S • Hydroxide, potassium • Formic acid • H2, Pt • PPh3=CH2 • KOtBu • |