Total Synthesis of (S)-Forphenicinol via Asymmetric Organocatalysis

Total Synthesis of (S)-Forphenicinol via Asymmetric Organocatalysis Full article

Journal

New Journal of Chemistry
ISSN: 1369-9261 , E-ISSN: 1144-0546

Output data

Year: 2023, Volume: 47, Number: 45, Pages: 20814-20817 Pages count : 4 DOI: 10.1039/d3nj04527g

Authors

Kovalevsky Ruslan ^1,2 , Kucherenko Alexander ² , Zlotin Sergei Grigorievich ²

Affiliations

1	M.V. Lomonosov Moscow State University, Department of Chemistry, Leninskie gory 1-3, 119234, Moscow, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991, Moscow, Russian Federation

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%).

Kovalevsky R. , Kucherenko A. , Zlotin S.G.
Total Synthesis of (S)-Forphenicinol via Asymmetric Organocatalysis
New Journal of Chemistry. 2023. V.47. N45. P.20814-20817. DOI: 10.1039/d3nj04527g WOS Scopus OpenAlex

Web of science:	WOS:001094511200001
Scopus:	2-s2.0-85176112266
OpenAlex:	W4387984609

DB	Citing
OpenAlex	3
Scopus	3
Web of science	3