Collect. Czech. Chem. Commun. 1985, 50, 1878-1887

Structure of laserolide and isolaserolide: Revision of constitution and determination of relative and absolute configuration

Miroslav Holuba, Miloš Buděšínskýa, Zdenka Smítalováa, David Šamana and Urszula Rychłewskab

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Laboratory of Crystallography, Department of Chemistry, Adam Mickiewicz University, Poznan, Poland


The position of the ester groups in sesquiterpenic lactones laserolide (I) and isolaserolide (II) has been revised and its relative and absolute configuration determined by chemical and physical methods (NMR and CD spectroscopy). The structure I was confirmed by X-ray diffraction analysis. Laserolide (I) is the first germacranolide found in the Umbelliferae family, isolaserolide (II) is the first representative of new stereostructural group of elemanolides - 5βH,6αH,7αH,10αCH3-elema-1,3-dien-6,12-olides.