Efficient and Scalable One-Pot Synthesis of 2,4-Dienols from Cycloalkenones: Optimized Total Synthesis of Valerenic Acid

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Abstract

A mild and selective one-pot procedure to provide 2,4-dienols from simple cycloalkenones in high yields is described. This transformation is based on the in situ formation of acid-labile allylic alcohols, which on treatment with trifluoroacetic acid undergo a formal [1,3]-hydroxy migration to form diastereo- and enantiomerically enriched 2,4-dienols. The usefulness of this protocol is demonstrated in a short synthesis of valerenic acid.

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