Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η3-allylpalladium intermediates.
A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework is formed via an η(3)-allylpalladium intermediate.
Department of Chemistry, School of Chemical Technology, Aalto University, P.O. Box 16100 (Kemistintie 1), FI-00076, Aalto, Finland.
Mikko
M
Passiniemi
Ari M P
AM
Koskinen
D000498:Allyl Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
D000498:Allyl Compounds; C468594:pachastrissamine; D010165:Palladium; D013110:Sphingosine