Total synthesis of (S)-forphenicinol via asymmetric organocatalysis.

Autor: Kovalevsky, R. A., Kucherenko, A. S., Zlotin, S. G.
Předmět:
Zdroj: New Journal of Chemistry; 12/7/2023, Vol. 47 Issue 45, p20814-20817, 4p
Abstrakt: Practical asymmetric synthesis of (S)-forphenicinol, the active ingredient of immunomodulator and anticancer drug Forfenimex®, from commercially available 2-hydroxy-dimethylterephthalate has been developed. Key steps of the synthesis are a stereogenic-center-forming enantioselective organocatalytic Mannich reaction of protected arylcarbaldimine with a kojic acid derivative and oxidative transformation of the γ-pyrone fragment into the carboxylic group. The total yield of (S)-forphenicinol hydrochloride (99% ee) via the proposed nine-step synthetic scheme (17%) is significantly higher than those attained by known methods (4.6% and 0.8%). [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index