Total synthesis of E-(γ)-Bisabolene:
| Reference: | Corey, E. J.; Seibel, W. L. Tetrahedron Lett., 1986, 27, 905. DOI |
| Reactions: | Cu-Vinyl+Alkyl-X • Allyl-X+Cu-R • B-Vinyl → Cu-Vinyl • Si-Vinyl+Allyl-X • Allyl-X+Si-R • Cyclohexene • Li-R → B-R • Borane+Li-R • Metalate rearrangement (B) • O-SiMe2tBu → O-H • Li/H → Li-Alkynyl • B-Alkynyl+Me3Si-OTf • |
| Reagents: | Alkynyl-BR2 • Alkyl-BR2 • BuLi(n) • CuI • Vinyl-Cu • MeI • Fluoride, R4N+ • TiCl4 • NHMePh • Vinyl-SiR3 • Alkynyl-BR2 • SiMe3-OTf • Vinyl-BR2 • Vinyl-SiR3 • HMPA (solvent) • |