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Synthesis 2010(17): 2979-2984  
DOI: 10.1055/s-0029-1218844
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of the α-d-Galactosyl Ceramide KRN7000 via an Organocatalytic Aldol Reaction as Key Step

Dieter Enders*, Violeta Terteryan, Jiří Paleček
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
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Publikationsverlauf

Received 19 May 2010
Publikationsdatum:
29. Juni 2010 (online)

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Abstract

The asymmetric synthesis of the antitumor and immunostimulatory α-d-galactosyl ceramide KRN7000 using a (R)-proline-catalyzed enantioselective aldol reaction as key step is described. The title compound is synthesized in thirteen linear steps with excellent stereoselectivity (de >98%, ee = 95%) employing the commercially available substrates 1-pentadecanal, 2,2-dimethyl-1,3-dioxan-5-one, hexacosanoic acid, and d-galactose.

Key words

α-galactosyl ceramide - asymmetric synthesis - aldol reaction - organocatalysis - proline

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