title: Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy.
abstract: 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.
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Patrick
authors.initials: P
authors.lastname: Wisse
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Mark A R
authors.initials: MA
authors.lastname: de Geus
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Gen
authors.initials: G
authors.lastname: Cross
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Adrianus M C H
authors.initials: AM
authors.lastname: van den Nieuwendijk
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Eva J
authors.initials: EJ
authors.lastname: van Rooden
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Richard J B H N
authors.initials: RJ
authors.lastname: van den Berg
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Johannes M F G
authors.initials: JM
authors.lastname: Aerts
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Jeroen D C
authors.initials: JD
authors.lastname: Codée
authors.affiliation: Gorleaus Laboratories, Leiden Institute of Chemistry, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis; D002384:Catalysis; D002518:Ceramides / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C092210:6-hydroxy-4-sphingenine; D000475:Alkenes; D002518:Ceramides; D020005:Propanols; C006463:allyl alcohol; D013110:Sphingosine