Total synthesis of Eupomatilone-6 (5-epi):
| Reference: | Hong, S.; McIntosh, M. C. Org. Lett. 2002, 4, 19. DOI |
| Reactions: | Pd/Sn-Aryl+Vinyl-X • Li-Vinyl+Ketone • Enone+Li-R • Enone epoxidation, nucleophilic • CompE+-Ketone/Epoxide+M-R • Enone → Enone-α-Halo • Quinone synthesis • Benzene synthesis • Claisen-Ireland • Epoxide → Allyl-OH • Lactone-5 • Epoxidation, dioxirane • CompOx-Alkene/Enone+Dioxirane • Benzene synthesis • |
| Reagents: | H2O2, K2CO3 • Br2 • Epoxide • Propenyl-Li • Acetic acid • Iodosobenzene-OAc • HOMe (react) • Aryl-SnR3 • Pd2(dba)3 • Epoxide • Mg° • Carbonate, potassium • Dioxirane • KN(SiMe3)2 • SiMe3-Cl • MeI • |