Total synthesis of Chorismic Acid Analog:
| Reference: | Mattia, K. M.; Ganem, B. J. Org. Chem. 1994, 59, 720. DOI |
| Reactions: | O-H → O-SiMe2tBu • Claisen-EnolEther • HWE → EnoateEster • Epoxide+M-SeR • Selenolate+Epoxide • Furst-Plattner diaxial • Epoxidation, peracid • Dehydrohalogenation → Enoate • Selenoxide-Ei → Allyl-OR • Selenide → Selenoxide • CarboxEster → CarboxEster(seleno) • |
| Reagents: | SiMe2tBu-Cl • SeMe-AlMe2 • NaOMe • Epoxide • Selenol, phenyl • BF3·OEt2 • Peracetic acid, trifluoro • Rh2(OAc)4 • LiNiPr2 • Formaldehyde • Selenolate, phenyl • Diazophosphonate • Imidazole • Dioxirane • |