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| - Total Synthesis of (±)-Kainic Acid with an Aza-[2,3]-WittigSigmatropic Rearrangement as the Key StereochemicalDetermining Step
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| - A flexible route to the kainoid skeleton is exemplified by the synthesis of (±)-kainic acid from3-butyn-1-ol. The route relies on the aza-[2,3]-Wittig sigmatropic rearrangement to efficiently installthe relative stereochemistry between C2−C3. The C4 stereocenter was derived from a diastereocontrolled iodolactonization. The aza-[2,3]-Wittig rearrangement potentially allows structuraldiversity at C3 and the displacement of the tosyloxy group with retention of stereochemistry allowsstructural diversity at C4. The trans-C2 carboxylic acid functional group was found to be the mostimportant for retention of stereochemistry at C4 upon treatment with a higher order cyano cupratereagent.
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