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Enantioselective Total Synthesis of (−)‐Diversonol
Authors:Prof. Dr. Lutz F. Tietze  Stefan Jackenkroll  Dr. Christian Raith  Dr. Dirk A. Spiegl  Johannes R. Reiner  Maria Claudia Ochoa Campos
Affiliation:Institute of Organic and Biomolecular Chemistry, Georg‐August‐University G?ttingen, Tammannstrasse 2, 37077 G?ttingen (Germany), Fax: (+49)?551‐39‐9476
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.
Keywords:asymmetric catalysis  domino reactions  palladium  total synthesis  Wacker oxidation
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