Asymmetric synthesis of (S)-dihydrokavain from l-malic acid |
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Authors: | Mustafa Eskici Abdullah Karanfil M. Sabih Özer Yalçın Kabak İnci Durucasu |
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Affiliation: | 1. Department of Chemistry, Faculty of Arts and Science, Manisa Celal Bayar University, Manisa, Turkey;2. mustafa.eskici@cbu.edu.tr;4. Department of Chemistry, Faculty of Arts and Science, Ordu University, Ordu, Turkey |
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Abstract: | A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination. |
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Keywords: | 1,2-Cyclic sulfates dihydrokavain lactonization triethylorthopropiolate |
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