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Circular dichroism of sesquiterpene-umbelliferone ethers and structure elucidation of a new derivative isolated from the gum resin “Asa Foetida”

Circulardichroismus von Sesquiterpen-Umbelliferon-Ethern und Strukturermittlung eines neuen Derivates aus dem Gummiharz “Asa Foetida”

  • Organische Chemie Und Biochemie
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Abstract

The CD spectra of 16 naturally occurring sesquiterpene-umbelliferone ethers, including the complete set of farnesiferol A isomers with all acetates and 6-oxoderivatives, are reported over the significant wavelength range of 350–200 nm. 11 compounds were isolated from an “Asa Foetida” sample and 5 further derivatives, already known as natural products, were obtained by acetylation orJones oxidation. In addition, a new compound — kamolonol (14) — was isolated. Its structure is characterized by twofold methyl migration in the drimenol derived sesquiterpene moiety.1H-NMR, MS, IR, UV, and CD data of the new compound are discussed.

Zusammenfassung

Es werden die CD-Spektren von 16 natürlich vorkommenden Sesquiterpen-Umbelliferon-Ethern, einschließlich Farnesiferol A mit allen Isomeren und allen Acetyl- bzw. 6-Oxo-Derivaten, im signifikanten Wellenlängenbereich von 350–200 nm beschrieben. Elf der Verbindungen wurden aus einem „Asa Foetida“-Präparat isoliert, fünf weitere bereits als Naturstoffe bekannte Derivate wurden mittels Acetylierung oderJones-Oxidation synthetisiert. Zusätzlich konnte eine neue Verbindung —Kamolonol (14) — isoliert werden, dessen Struktur durch zweifache Methylgruppenwanderung im Drimenyl-Sesquiterpenanteil charakterisiert ist. Die Strukturemittlung erfolgte mittels spektroskopischer Methoden (1H-NMR, MS, IR, UV und CD).

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Authors and Affiliations

  1. Institute of Organic Chemistry, University of Vienna, A-1090, Wien, Austria

    Otmar Hofer & Michael Widhalm

  2. Institute of Botany, University of Vienna, A-1030, Wien, Austria

    Harald Greger

Authors
  1. Otmar Hofer
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  2. Michael Widhalm
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  3. Harald Greger
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Herrn Prof. Dr.K. Schlögl mit den besten Wünschen zum 60. Geburtstag gewidmet.

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Hofer, O., Widhalm, M. & Greger, H. Circular dichroism of sesquiterpene-umbelliferone ethers and structure elucidation of a new derivative isolated from the gum resin “Asa Foetida”. Monatsh Chem 115, 1207–1218 (1984). https://doi.org/10.1007/BF00809352

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  • DOI: https://doi.org/10.1007/BF00809352

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