Total synthesis of Ethisolide:
| Reference: | Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228-2235. DOI |
| Reactions: | Sulfoxide-Ei → EneLactone • Mitsunobu → OC(O)R • Allyl-OH → Allyl-OC(O)R • O-SEM → O-H • CarboxAcid → CarboxEster • ConjAdd M-SR • Enone+Thiolate • Claisen-Ireland • Aldehyde+CarboxEster enolate • Lactone-5 • Lactone-5 • Sulfide → Sulfoxide • Dehydronitration → EnoateEster • CarboxEster → Ketene acetal • |
| Reagents: | LiN(SiMe3)2 • SiMe3-Cl • PPh3, DEAD • Sulfonic acid, Camphor • Carbonate, potassium • DBU • HF • BF3·OEt2 • Thiolate, phenyl • Diazomethane • Perbenzoic acid, 3-chloro • |