Synthesis of the proposed structure of queenslandon |
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Authors: | Vaidotas Navickas |
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Institution: | Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany |
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Abstract: | The proposed structure of the benzolactone queenslandon (6) was synthesized utilizing a triol containing building block prepared from d-ribose. While a ring-closing metathesis approach did not lead to the macrocycle, alkylation of a benzyl(phenyl)selane, elimination to generate the styrene double bond, followed by Mitsunobu macrolactonization proved to be successful. Spectral data suggest that the structure of queenslandon should be revised, probably to the C11 epimer. |
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Keywords: | Benzolactone Cross metathesis Mitsunobu macrolactonization Chiron approach |
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