Total synthesis of Dehydroarachidonic Acid.:
| Reference: | Corey, E. J.; Kang, J. Tetrahedron Lett., 1982, 23, 1651. DOI |
| Reactions: | Cu-Vinyl+Allenyl-X • Allenyl-X+Cu-R • Li/Sn → Li-Vinyl • Hydroboration Alkyne • Alkyne → Ene-cis (B-H) • B-Vinyl → H-Vinyl • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • Alkyl-X+Li-R • Li/I → Li-Vinyl • Hydrostannation Alkyne • Si-Propargyl → I-Allenyl • Sn-Vinyl → I-Vinyl • Cu-Vinyl+Allenyl-I • Allenyl-X+Cu-R • |
| Reagents: | Vinyl-SnR3 • BuLi(n) • I2 • BH(Siam)2 • Acetic acid • BuLi(tert) • CuI·SMe2 • Allenyl-I • Alkynyl-Li • I2 • AgOAc • SiMe3-CH2X • HMPA (solvent) • HSnBu2H • Vinyl-SnR3 • Vinyl-Li • CuI·SMe2 • Allenyl-I • |