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Gold Catalysis: Efficient Synthesis and Structural Assignment of Jungianol and epi-Jungianol

Authors

  • A. Stephen K. Hashmi Prof. Dr.,

    1. Institut für Organische Chemie Universität Stuttgart Pfaffenwaldring 55, 70569 Stuttgart, Germany, Fax: (+49) 711-685-4321
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  • Li Ding Dr.,

    1. Institut für Organische Chemie Universität Stuttgart Pfaffenwaldring 55, 70569 Stuttgart, Germany, Fax: (+49) 711-685-4321
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  • Jan W. Bats Dr.,

    1. Institut für Organische Chemie und Chemische Biologie Johann Wolfgang Goethe-Universität Frankfurt am Main Marie-Curie-Strasse 11, 60439 Frankfurt, Germany
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    • Crystallographic investigation.

  • Peter Fischer Dr.,

    1. Institut für Organische Chemie Universität Stuttgart Pfaffenwaldring 55, 70569 Stuttgart, Germany, Fax: (+49) 711-685-4321
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  • Wolfgang Frey Dr.

    1. Institut für Organische Chemie Universität Stuttgart Pfaffenwaldring 55, 70569 Stuttgart, Germany, Fax: (+49) 711-685-4321
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    • Crystallographic investigation.


Abstract

Starting from 2-methylfuran and crotonaldehyde, both jungianol and epi-jungianol were prepared by a six-step sequence including a gold-catalyzed arene synthesis and a photochemical SN2-like reduction with lithium aluminum hydride. Not a single protective group was needed in the entire synthesis. With both diastereomers in hand, the stereochemical assignment in the literature could be corrected by means of a thorough 1H NMR spectroscopic analysis and an X-ray diffraction study on an epi-jungianol derivative.

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