Total synthesis of Artimisinin (Avery):
| Reference: | Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629-4632. DOI |
| Reactions: | Claisen-Ireland • Shapiro reaction • Li-Vinyl+CarboxAmide • CarboxAmide+Li-R • Mechanism • Lactone-6 • Ozonolysis • KetoSulfoxide dianion+Alkyl-X • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • CarboxEster → CarboxAcid • Ketone → Hydrazone • Ketone-α-S(O)nR → Ketone • Ketone → Ketone-α-SR • Sulfide → Sulfoxide • Al-SiR3+Enal • O-H → O-C(O)R • CarboxAcid → CarboxEster • Williamson esterification • Alkyl-X+Enolate • CarboxEster enolate+Alkyl-X • Ketal → Ketone • |
| Reagents: | LiNiPr2 • Disulfide, phenyl • Al(Hg) • Hydrazine, tosyl • BuLi(n) • Al(SiMe3)3 • Acetic anhydride, DMAP • LiNiPrCy • Carbonate, potassium • LiNiPrCy • Hydroxide, potassium • Oxalic acid • O3 • Perbenzoic acid, 3-chloro • LiNiPr2 • MeI • DMF (react) • |