A modified approach to the phomoidrides: synthesis of a late-stage intermediate containing a key carbon quaternary stereocenter |
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Authors: | Bastien Castagner |
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Institution: | Department of Chemistry, Columbia University, 3000 Broadway, MC 3117, New York, NY 10027, United States |
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Abstract: | A previously developed approach to the synthesis of the phomoidrides has been modified to incorporate all necessary carbon atoms prior to the key tandem carbonylation/Cope rearrangement reaction. This modification necessitated the synthesis of a challenging all-carbon quaternary stereocenter, which in turn rendered ineffective several reactions from the original synthesis. An oxidative radical cleavage of a spirocyclopropane ring system was developed that accomplishes the synthesis of the quaternary center, and a regioselective double hydroboration reaction was devised that provides an alternate approach to a key sequence of functional group interconversions, where the originally developed route was found to be ineffective. |
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Keywords: | Phomoidrides Quaternary stereocenter Radical Hydroboration |
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