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Stereoselective Synthesis of Enantiomerically Pure Nupharamine Alkaloids from Castoreum

Authors

  • Alexander Stoye,

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • Gabriele Quandt,

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • Björn Brunnhöfer Dr.,

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • Elissavet Kapatsina,

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • Julia Baron,

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • André Fischer,

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • Markus Weymann Dr.,

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • Horst Kunz Prof. Dr.

    1. Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-24786
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  • This work was supported by the Fonds der Chemischen Industrie. B.B. and M.W. are grateful to the Fonds der Chemischen Industrie for a predoctoral fellowships.

Abstract

An animalic note: The first total synthesis of the all-cis nupharamine 2, an alkaloid from beaver castoreum, is based on the stereoselective domino Mannich–Michael reaction of N-galactosylfurylaldimine to give 1 (Piv=pivaloyl), subsequent conjugate cuprate addition, and stereoselective protonation of the enolate. These reactions are all controlled by the carbohydrate. Protonation of the enolate after cleavage of the auxiliary leads to epimer 3.

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