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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 18
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Articles

Asymmetric synthesis of (S)-dihydrokavain from l-malic acid

, , , &
Pages 2382-2390 | Received 07 May 2018, Published online: 08 Oct 2018
 

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.

Graphical Abstract

Additional information

Funding

The authors gratefully acknowledge Manisa Celal Bayar University for financial support through a project (FBE-2007-064). Manisa Celal Bayar University as the founder of our work to the Open Funder Registry data base.

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