Total synthesis of Zearalenone (Hegedus):
| Reference: | Kalivretenos, A.; Stille, J, K,; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. DOI |
| Reactions: | O-SiMe2tBu → O-H (phenol) • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Cu-Vinyl+Epoxide • Epoxide+Cu-R • Mg-R → Cu-R • Hydroboration → Alkyl-OH • Mg-Alkyl+Aldehyde • Aldehyde+Mg-R • Li/H → Li-Aryl • O-MEM → O-H • Pd/Sn-Vinyl+Aryl-X • Lactone-9+ • Alkyl-OH → Alkyl-Br • Appel → Br • CarboxAmide → CarboxEster • Li-Aryl → I-Aryl • O-H → O-MEM • CarboxEster → CarboxAcid • Corey-Kim • Alkyl-OH → Aldehyde • Mitsunobu → OC(O)R • Alkyl-OH → Alkyl-OC(O)R • |
| Reagents: | Aryl-Li • BuLi(tert) • ICl • Me3O+ X- • Carbonate, sodium • MEM-Cl • Hydroxide, lithium • Epoxide • Vinyl-MgX • CuI • SiMe2tBu-Cl • BH-BBN • PPh3, CBr4 • Alkyl-MgX • Mg° • NCS • Fluoride, R4N+ • PPh3, DEAD • Pd(PPh3)4 • HCl, H2O • Alkyl-MgX • |