Total synthesis of Kainic Acid:
| Reference: | Morita, Y.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2005, 7, 4337-4340 DOI |
| Reactions: | O-H → O-C(O)R • N-Bn → N-C(O)OR • Nitrile → CarboxAmide • Singlet oxygen+Diene • Furan+Singlet oxygen • Julia-Lythgoe • Ketone → C=CH2 • Reductive elimination - S/OR • Li/H → Li-Amine (asym) • Azomethine ylide Cycloaddition • Amine-5 • Nitrile → CarboxAcid • Li-Sulfone+Ketone • Li-Me+Lactone • Lactone+Li-R • Mechanism • O-H → O-C(O)R (asym) • Reductive etherification • O-H → O-MOM • N-C(O)OR → N-H • N-H → N-Boc • Li-Amine+CO2 • CarboxAcid → CarboxEster • Williamson esterification • O-MOM → O-H • Alkyl-OH → Alkyl-Br • Appel → Br • Alkyl-X → Alkyl-CN • Cyanide+Alkyl-X • N-Boc → N-H • CarboxEster → CarboxAcid • |
| Reagents: | O2 (singlet) • Rose Bengal • Lipase • Vinyl-OAc • Acetic acid, trifluoro • O=C(OMe)Cl • HSiEt3 • Me-Li • 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 • |