Synthesis of 6‑Hydroxysphingosine and α‑Hydroxy Ceramide Using a Cross-Metathesis Strategy

In this paper, a new synthetic route toward 6-hydroxysphingosine and α-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupli...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-07, Vol.80 (14), p.7258-7265
Main Authors: Wisse, Patrick, de Geus, Mark A. R, Cross, Gen, van den Nieuwendijk, Adrianus M. C. H, van Rooden, Eva J, van den Berg, Richard J. B. H. N, Aerts, Johannes M. F. G, van der Marel, Gijsbert A, Codée, Jeroen D. C, Overkleeft, Herman S
Format: Article
Language:English
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Summary:In this paper, a new synthetic route toward 6-hydroxysphingosine and α-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00823