Journal
SYNTHETIC COMMUNICATIONS
Volume 48, Issue 18, Pages 2382-2390Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2018.1489057
Keywords
1; 2-Cyclic sulfates; dihydrokavain; lactonization; triethylorthopropiolate
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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. [GRAPHICS] .
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