Total synthesis of Z-(γ)-Bisabolene:
| Reference: | Corey, E. J.; Seibel, W. L. Tetrahedron Lett., 1986, 27, 909. DOI |
| Reactions: | Cu-Vinyl+Alkyl-X • Allyl-X+Cu-R • B-Alkynyl+Alkyl-X • Alkyl-X+B-R • Cyclohexene • B-Vinyl → Cu-Vinyl • Li-R → B-R • Borane+Li-R • Metalate rearrangement (B) • Allyl-OH → Allyl-Br • Li/H → Li-Alkynyl • |
| Reagents: | PhLi • PPh3, Br2 • Alkyl-BR2 • BuLi(n) • CuI • P(OEt)3 • MeI • HMPA (solvent) • Alkynyl-BR2 • CuOTf • PPh3 • HMPA (solvent) • |