Enantioselective Total Synthesis of (−)‐Diversonol |
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Authors: | Prof. Dr. Lutz F. Tietze Stefan Jackenkroll Dr. Christian Raith Dr. Dirk A. Spiegl Johannes R. Reiner Maria Claudia Ochoa Campos |
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Affiliation: | Institute of Organic and Biomolecular Chemistry, Georg‐August‐University G?ttingen, Tammannstrasse 2, 37077 G?ttingen (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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Keywords: | asymmetric catalysis domino reactions palladium total synthesis Wacker oxidation |
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