New Journal of Chemistry
New Journal of Chemistry
10 months ago

Total Synthesis of (S)-Forphenicinol via Asymmetric Organocatalysis

Ruslan Kovalevsky, Alexander Kucherenko, Sergei Grigorievich Zlotin
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%).

Publisher URL: http://pubs.rsc.org/en/content/articlepdf/2023/NJ/D3NJ04527G

DOI: 10.1039/d3nj04527g

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