Stereoselective syntheses of the three isomers of ethylene glycol bis(tropane-3-carboxylate).
Three epimers of ethylene glycol bis(tropane-3-carboxylate) (3alpha,3alpha'-, 3alpha,3beta'-, 3beta,3beta'-) have been synthesized by starting from 3-tropinone. 3-Tropinone was converted into the corresponding enol triflate and then subjected to palladium-catalyzed alkoxycarbonylation to provide the key intermediate methyl trop-2-ene-3-carboxylate in good yield. Stereoselective routes were developed to afford the three stereoisomers of ethylene glycol bis(tropane-3-carboxylate).
Cheng
Jie
J
Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.
Moore
Zakhia
Z
Stevens
Edwin D
ED
Trudell
Mark L
ML
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D005026:Ethylene Glycols / Q000138:chemical synthesis*; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry*
D005026:Ethylene Glycols; D008024:Ligands; D014326:Tropanes; C470773:ethylene glycol bis(tropane-3-carboxylate); D010165:Palladium