Total synthesis of Cerulenin (Corey):
| Reference: | Corey, E. J.; Williams, D. R. Tetrahedron Lett., 1977, 3847. DOI |
| Reactions: | Li/Sn → Li-Vinyl • Li-Vinyl+Alkyl-X • Allyl-X+Li-R • Li/I → Li-Alkyl • Hydrostannation Alkyne • Alkyl-X → Alkyl-I • Finkelstein reaction • O-THP → O-H • O-H → O-SO2Me • Li-Alkyl+CarboxAnhydride • CarboxAcid → CarboxEster • CarboxEster → CarboxAmide • Li/Sn → Li-Vinyl • |
| Reagents: | Vinyl-SnR3 • Alkyl-Li • HSnBu3 • AIBN • BuLi(n) • Acetic acid • BuLi(tert) • Diazomethane • Sulfonyl chloride, methane, NEt3 • Iodide, sodium • Allyl-Br • |