Total synthesis of Limonin (Part 2) New:
| Reference: | Yamashita, S.; Naruko, A.; Nakazawa, Y.; Zhao, L.; Hayashi, Y.; Hirama, M. Angew. Chem. Int. Ed. 2015, 54, 8538-8541. DOI (Part 1) |
| Reactions: | Saegusa oxidation • Ketone → Enone • EnolSilane → Enone • Ketone → EnolSilane • Enone → EnolTriflate • Pd/Sn-Vinyl+Vinyl-X • Singlet oxygen+Diene • Bicyclo(222)-oxa • Lactone → Lactol • Furan synthesis • Peroxide rearrangement • Pinacol • Ketone epimerization • Baeyer-Villiger • Lactone-6 • O-SiEt3 → O-H • CompE+-Si-O/Si-O+H2O • Radical oxygenation • Ether-5 • Lactone-6 • O-SiMe3 → O-H • Alkyl-OH → Ketone • |
| Reagents: | LiN(SiMe3)2 • SiMe3-Cl • Pd(OAc)2 • Tf2O • Pyridine, 2,6-di-tBu • O2 (singlet) • Photochemistry • AlHiBu2 • CuCl • Acetic anhydride, DMAP • PPh3 • SiO2 • DBU • H2O2 • Fluoride, R4N+ • Iodosobenzene-OAc • I2 • Photochemistry • Fluoride, R4N+ • RuO4-Pr4N+, NMO • Sieves • Chloride, lithium • |