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Enantioselective Total Synthesis of (−)-Diversonol

Authors

  • Prof. Dr. Lutz F. Tietze,

    Corresponding author
    1. Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-9476
    • Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-9476
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  • Stefan Jackenkroll,

    1. Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-9476
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  • Dr. Christian Raith,

    1. Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-9476
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  • Dr. Dirk A. Spiegl,

    1. Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-9476
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  • Johannes R. Reiner,

    1. Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-9476
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  • Maria Claudia Ochoa Campos

    1. Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-9476
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Abstract

For the synthesis of (−)-diversonol (ent-1), an enantioselective domino-Wacker/carbonylation/methoxylation reaction and an enantioselective Wacker oxidation were used to give the chroman in high yield and 96 % and 93 % ee, respectively. Dihydroxylation at the vinyl moiety using the Sharpless procedure and a Wittig–Horner reaction followed by hydrogenation, benzylic oxidation, and an intramolecular acylation provided the tetrahydroxanthenone, from which ent-1 is accessible in a few steps. Furthermore, the synthesis of the diastereomeric diversonol rac-1,9 a-epi-diversonol (rac-41) is also described.

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