Chemo-enzymatic enantioconvergent approach toward ethyl shikimate from ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate

Yasunobu Yamashita, Kengo Hanaya, Takeshi Sugai, Tohru Mizushima, Mitsuru Shoji

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

An enantioconvergent route for natural form of ethyl shikimate was achieved from Diels-Alder adduct of furan and acryloyl chloride. The key step was a highly enantioselective (E >500) and efficient acetylation of ethyl (3R*,4S*,5S*)-5-hydroxy-3,4-isopropylidenedioxycyclohex-1- enecarboxylate, which had a diastereomeric relationship with ethyl shikimate, mediated by Burkholderia cepacia lipase (Amano PS-IM). Both of the resolved enantiomers were converted to natural form of ethyl shikimate by inversion at C-5 for the former and at C-3 and C-4 for the latter, respectively.

Original languageEnglish
Pages (from-to)6527-6532
Number of pages6
JournalTetrahedron
Volume69
Issue number31
DOIs
Publication statusPublished - 2013 Aug 5

Fingerprint

Burkholderia cepacia
Acetylation
Enantiomers
Lipase
furan
acryloyl chloride

Keywords

  • Carbacycle
  • Enantioconvergent approach
  • Ethyl shikimate
  • Kinetic resolution
  • Lipase

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chemo-enzymatic enantioconvergent approach toward ethyl shikimate from ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate. / Yamashita, Yasunobu; Hanaya, Kengo; Sugai, Takeshi; Mizushima, Tohru; Shoji, Mitsuru.

In: Tetrahedron, Vol. 69, No. 31, 05.08.2013, p. 6527-6532.

Research output: Contribution to journalArticle

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