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Synthesis 2006(5): 753-755  
DOI: 10.1055/s-2006-926342
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of the Immunosuppressive Agent FTY720

Sanghee Kim*a,b, Hyeseung Leea,b, Minhee Leea,b, Taeho Leeb
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;
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Publikationsverlauf

Received 1 September 2005
Publikationsdatum:
08. Februar 2006 (online)

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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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See http://www.transplantationschweiz.ch/d/fty720/ for more information.