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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 • Acetal → ether • 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 • Ketone → C=CH2 • 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 • SiMe3-OTf • HgCl2 • Hydroxide, potassium • Boc2O • Chloromethyl ether • BuLi, Sparteine • BuLi(sec) • CO2 • Carbonate, potassium • Acetyl chloride • PPh3, CBr4 • Cyanide, potassium • H2O2, NaOH • Hydroxide, potassium • Acetic acid, trifluoro • Iodide,R4N+ • NEtiPr2 • Photochemistry • Acetic acid, trifluoro •

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