image

Total synthesis of Kainic Acid:
Reference: Morita, Y.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2005, 7, 4337-4340 DOI
Keywords: O-H -> O-C(O)R • N-H -> N-C(O)OR • N-C(O)OR -> N-H • N-H -> N-Boc • O-H -> O-MOM • Williamson esterification • Alkyl-OH -> Alkyl-Br • CarboxEster -> CarboxAcid • N-Boc -> N-H • Singlet oxygen+Diene • Furan+Singlet oxygen • Julia-Lythgoe • Li/H(asym) -> Li-Amine • Azomethine ylide Cycloaddition • Amine-5 • Nitrile -> CarboxAcid • Li-Sulfone+Ketone • Alkyl-X -> Alkyl-CN • Li-Me+Lactone • Lactone+Li-R • Mechanism •
Reagents: O2 (singlet) • Rose Bengal • Lipase • Vinyl-OAc • Acetic acid, trifluoro • O=C(OR)Cl • HSiEt3 • MeLi • LiCH2-Sulfonyl • Acetic anhydride • HgCl2 • Hydroxide, potassium • Boc2O • Cl-CH2-OR • BuLi, Sparteine • BuLi(sec) • CO2 • Carbonate, potassium • Acetyl chloride • PPh3, CBr4 • Cyanide, potassium • H2O2, NaOH • Hydroxide, potassium • Acetic acid, trifluoro • Iodide, Bu4N+ • NEtiPr2 • Photochemistry • Acetic acid, trifluoro •

Syntheses Home