Total synthesis of ( S )-forphenicinol via asymmetric organocatalysis

Total synthesis of ( S )-forphenicinol via asymmetric organocatalysis

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 organocatalyti...

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Veröffentlicht in:New journal of chemistry 2023-11, Vol.47 (45), p.20814-20817
Hauptverfasser: Kovalevsky, R. A., Kucherenko, A. S., Zlotin, S. G.
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Asymmetry
Enantiomers
Immunomodulators
Synthesis
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container_issue 45
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container_title New journal of chemistry
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creator Kovalevsky, R. A.
Kucherenko, A. S.
Zlotin, S. G.
description 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%).
doi_str_mv 10.1039/D3NJ04527G
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Asymmetry
Enantiomers
Immunomodulators
Synthesis
title Total synthesis of ( S )-forphenicinol via asymmetric organocatalysis
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