Total synthesis of (-)-(alpha)-kainic acid via a diastereoselective methylenecyclopropane ring expansion |
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Authors: | Scott Mark E Lautens Mark |
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Institution: | Davenport Research Laboratories, Department of Chemistry, University of Toronto, Ontario, Canada. |
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Abstract: | reaction: see text] A concise and enantioselective synthesis of (-)-(alpha)-kainic acid in 13 steps with an overall yield of 15% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with excellent diastereoselectivity (>20:1) via a MgI(2)-mediated ring expansion of a tertiary methylenecyclopropyl amide. A selective hydroboration was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(alpha)-kainic acid. |
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