Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy

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2015
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Ibrom, Kerstin
Dickschat, Jeroen S.
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Feeding of (2,3,4,5,6-13C5)mevalonolactone to the fungus Hypomyces odoratus resulted in a completely labeled sesquiterpene ether. The connectivity of the carbon atoms was easily deduced from a 13C,13C COSY spectrum, revealing a structure that was different from the previously reported structure of hypodoratoxide, even though the reported 13C NMR data matched. A structural revision of hypodoratoxide is thus presented. Its absolute configuration was tentatively assigned from its co-metabolite cis-dihydroagarofuran. Its biosynthesis was investigated by feeding of (3-13C)- and (4,6-13C2)mevalonolactone, which gave insights into the complex rearrangement of the carbon skeleton during terpene cyclization by analysis of the 13C,13C couplings.

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ISO 690BARRA, Lena, Kerstin IBROM, Jeroen S. DICKSCHAT, 2015. Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy. In: Angewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765
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@article{Barra2015-05-26Struc-57617,
  year={2015},
  doi={10.1002/anie.201501765},
  title={Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by <sup>13</sup>C,<sup>13</sup>C COSY NMR Spectroscopy},
  number={22},
  volume={54},
  issn={1433-7851},
  journal={Angewandte Chemie International Edition},
  pages={6637--6640},
  author={Barra, Lena and Ibrom, Kerstin and Dickschat, Jeroen S.}
}
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    <dcterms:abstract xml:lang="eng">Feeding of (2,3,4,5,6-&lt;sup&gt;13&lt;/sup&gt;C&lt;sub&gt;5&lt;/sub&gt;)mevalonolactone to the fungus Hypomyces odoratus resulted in a completely labeled sesquiterpene ether. The connectivity of the carbon atoms was easily deduced from a &lt;sup&gt;13&lt;/sup&gt;C,&lt;sup&gt;13&lt;/sup&gt;C COSY spectrum, revealing a structure that was different from the previously reported structure of hypodoratoxide, even though the reported 13C NMR data matched. A structural revision of hypodoratoxide is thus presented. Its absolute configuration was tentatively assigned from its co-metabolite cis-dihydroagarofuran. Its biosynthesis was investigated by feeding of (3-&lt;sup&gt;13&lt;/sup&gt;C)- and (4,6-&lt;sup&gt;13&lt;/sup&gt;C&lt;sub&gt;2&lt;/sub&gt;)mevalonolactone, which gave insights into the complex rearrangement of the carbon skeleton during terpene cyclization by analysis of the &lt;sup&gt;13&lt;/sup&gt;C,&lt;sup&gt;13&lt;/sup&gt;C couplings.</dcterms:abstract>
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