Stereochemical assignment of the fungal metabolite xestodecalactone A by total synthesis |
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| Authors: | Gerhard Bringmann Gerhard Lang Manuela Michel Markus Heubes |
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| Affiliation: | Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany |
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| Abstract: | The first synthesis of the macrocyclic natural product xestodecalactone A, a metabolite of a sponge-derived fungus, is described. By the use of methyl 5-hydroxyhexanoate in its R- or S-configured form, or as its racemate as the precursors, both enantiomers of xestodecalactone A as well as the racemic compound were obtained. Comparison of these synthetic products with the natural product by circular dichroism (CD) spectroscopy and by HPLC on a chiral phase revealed the natural product to have the (R)-configuration. |
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| Keywords: | Xestodecalactones Total synthesis Absolute configuration Natural products Chiral phase Circular dichroism spectroscopy |
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