An expeditious stereoselective synthesis of natural (-)-Cassine via cascade HWE [3 + 2]-cycloaddition process.
l-Rhamnose is transformed to (-)-Cassine via a remarkable four step one pot reaction. The Horner-Wadsworth-Emmons [3 + 2]-1,3-dipolar cycloaddition reaction cascade is the pivotal step in this reaction sequence and makes the synthesis highly efficient.
Herdeis
Claus
C
Institut für Pharmazie und Lebensmittelchemie der Universität Würzburg, Am Hubland, 97074, Würzburg, Germany. herdeis@pharmazie.uni-wuerzburg.de
Küpper
Patrick
P
Plé
Sophie
S
D002366:Cassia / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D010880:Piperidines; C426663:cassine