Total synthesis of 5-Desoxy-Leucotriene D:
| Reference: | Corey, E. J.; Hoover, D. J. Tetrahedron Lett., 1982, 23, 3463. DOI |
| Reactions: | O-H → O-C(O)R • O-C(O)R → O-H • 2,3-Sigmatropic Sulfoxide • Pummerer • Acetal(thio) → Aldehyde • Wittig-alkyl → Ene-cis • CompE+-Aldehyde/CarboxEster+Wittig • Allyl-X → Allyl-SR • Mechanism • Li-Allyl+Aldehyde • CompE+-Aldehyde/CarboxEster+M-R • Li-Sulfoxide+Aldehyde • O-H → O-SO2Me • Allyl-X → Allyl-SR • Sulfide → Sulfoxide • CarboxEster → CarboxAcid • Alkyl-X → Alkyl-SR • |
| Reagents: | BuLi(n) • Benzoyl chloride • Acetic anhydride, trifluoro • Acetate, sodium • Allyl-Br • Carbonate, potassium • Carbonate, calcium • HgCl2 • PPh3 • Carbonate, potassium • Sulfonyl chloride, methane, NEt3 • Carbonate, potassium • Hydroxide, lithium • Perbenzoic acid, 3-chloro • |