Efficient Synthesis of the Immunosuppressive Agent FTY720

Sanghee Kim; Hyeseung Lee; Minhee Lee; Taeho Lee

doi:10.1055/s-2006-926342

SHORTPAPER

Efficient Synthesis of the Immunosuppressive Agent FTY720

Sanghee Kim*^a,b, Hyeseung Lee^a,b, Minhee Lee^a,b, Taeho Lee^b
^a College of Pharmacy, Seoul National University, San 56-1, Shilim Kwanak, Seoul 151-742, Korea
^b Natural Products Research Institute, College of Pharmacy, Seoul National University, 28 Yungun, Jongro, Seoul 110-460, Korea
Fax: +82(2)7628322; e-Mail: pennkim@snu.ac.kr;

Abstract

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Abstract

The concise and practical synthesis of the biologically important FTY720 was achieved employing the palladium-catalyzed Sonogashira coupling reaction as a key step. The commercial tris(hydroxymethyl)aminomethane was converted to alkyne 2 via a three-step synthesis. The coupling reactions of alkyne 2 with aryl iodide 3, followed by subsequent hydrogenation of the internal alkyne and removal of the protecting groups provided FTY720 in high overall yield.

Key words

cross-coupling - synthesis - FTY720 - immunosuppressants - alkynes

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References

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