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

研究成果: Article査読

6 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)6527-6532
ページ数6
ジャーナルTetrahedron
69
31
DOI
出版ステータスPublished - 2013 8 5

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

フィンガープリント 「Chemo-enzymatic enantioconvergent approach toward ethyl shikimate from ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル