Chemo-enzymatic synthesis of (R,R)-(-)-Pyrenophorin

Takeshi Sugai, Osamu Katoh, Hiromichi Ohta

研究成果: Article査読

54 被引用数 (Scopus)

抄録

A chemo-enzymatic approach to (R,R)-(-)-pyrenophorin starting from commercially available 6-methyl-5-hepten-2-one is described. Firstly, (R)-6-methyl-5-hepten-2-ol (sulcatol) was prepared by interface-bioreactor mediated asymmetric reduction of the corresponding ketone by a yeast, Pichia farinosa IAM 4682 (51% yield, 90%e.e.). The sequential carbon-chain elongation via Horner-Emmons olefination of protected aldehyde and cyanation afforded all of carbon skeleton in the seco acid with a desired β,γ-(E)-double bond. By the aid of a microorganism, Rhodococcus rhodochrous IFO15564, the nitrile was efficiently hydrolyzed to give the corresponding carboxylic acid, (R,E)-7-hydroxy-3-octenoate, the key synthetic intermediate without affecting the position and configuration of the double bond (90% yield). Dimeric lactone structure was obtained by utilizing a lipase-catalyzed lactonization. While Pseudomonas cepacia lipase-catalyzed reaction worked in a moderate efficiency, higher yield of desired dimeric lactone (44%) was obtained by the use of an immobilized form of Candida antarctica lipase. The lactonization was accelerated in the presence of molecular sieves 4A. (R,R)-(-)-Pyrenophorin was obtained from this dimeric lactone (Seebach's intermediate) by the subsequent chemical transformation.

本文言語English
ページ(範囲)11987-11998
ページ数12
ジャーナルTetrahedron
51
44
DOI
出版ステータスPublished - 1995 10 30

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「Chemo-enzymatic synthesis of (R,R)-(-)-Pyrenophorin」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