Total synthesis of allo-Kainic Acid:
| Reference: | DeShong, P.; Kell, D. A. Tetrahedron Lett. 1986, 27, 3979. DOI |
| Reactions: | O-SiMe2tBu → O-H • CarboxAcid → CarboxEster • Wittig-methyl • CompE+-Ketone/CarboxEster+Wittig • N-Bn → N-H • Azomethine ylide Cycloaddition • Amine-5 • Electrocyclic-4π • Jones oxidation • Alkyl-OH → CarboxAcid • CarboxEster → CarboxAcid • |
| Reagents: | PPh3=CH2 • Fluoride, R4N+ • CrO3, H2SO4 (Jones) • Diazomethane • Hydroxide, sodium • O=C(OR)Cl • Aziridine • |