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

ESKİCİ M., Karanfil A., ÖZER M. S., Kabak Y., Durucasu İ.

Synthetic Communications, cilt.48, sa.18, ss.2382-2390, 2018 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 48 Sayı: 18
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1080/00397911.2018.1489057
  • Dergi Adı: Synthetic Communications
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2382-2390
  • Anahtar Kelimeler: 1,2-Cyclic sulfates, dihydrokavain, lactonization, triethylorthopropiolate
  • Manisa Celal Bayar Üniversitesi Adresli: Evet

Özet

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.