Structure of isosilerolide, relative and absolute configuration of silerolide and lasolide - Sesquiterpenic lactones of new stereoisomeric type of eudesmanolides
Miroslav HolubInstitute of Organic Chemistry and Biochemistry, Czechoslovak Academ of Sciences, 166 10 Prague 6, CzechoslovakiaMiloš Buděšı́nskýInstitute of Organic Chemistry and Biochemistry, Czechoslovak Academ of Sciences, 166 10 Prague 6, CzechoslovakiaZdeňka SmítalovǎInstitute of Organic Chemistry and Biochemistry, Czechoslovak Academ of Sciences, 166 10 Prague 6, CzechoslovakiaDavid ŠamanInstitute of Organic Chemistry and Biochemistry, Czechoslovak Academ of Sciences, 166 10 Prague 6, CzechoslovakiaUrszula RychłewskaLaboratory of Crystallography, Department of Chemistry, Adam Mickiewicz University, Poznan, Poland
1986en
ABI
Abstract
On the basis of spectroscopic, particularly 1 H NMR data, isosilerolide was assigned structure I , including the absolute configuration. The structure was confirmed by X-ray diffraction. Isosilerolide represents a new stereoisomeric type of natural eudesmanolides, characterized as 5βH, 6αH, 7αH, 10αCH 3 -eudesman-6,12-olide. As shown by the chemical correlation of isosilerolide ( I ) with silerolide ( III ) and lasolide ( X ), the latter two natural lactones belong to this stereoisomeric group of eudesmanolides. Analysis of models and 1 H NMR data shows that structures of some eudesman-6,12-olides, published by other authors, should be corrected.
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