Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin

Hiromichi Ohta, Yoichi Kimura, Yasushi Sugano, Takeshi Sugai

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

Kinetic resolution of racemic 1-cyano-1-methylalkyl and alkenyl acetates has been achieved on incubation with Pichia miso IAM 4682, which hydolyzed selectively the (R)-enantiomer, leaving behind the (S)-enantiomer intact. The chiral 1-cyano-1-methyl-5-hexenyl acetate thus obtained was converted to (S)-(-)-frontalin via unsaturated diol.

Original languageEnglish
Pages (from-to)5469-5476
Number of pages8
JournalTetrahedron
Volume45
Issue number17
DOIs
Publication statusPublished - 1989

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Enantiomers
Acetates
Soy Foods
Kinetics
Pichia
cyanohydrin
frontalin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin. / Ohta, Hiromichi; Kimura, Yoichi; Sugano, Yasushi; Sugai, Takeshi.

In: Tetrahedron, Vol. 45, No. 17, 1989, p. 5469-5476.

Research output: Contribution to journalArticle

Ohta, Hiromichi ; Kimura, Yoichi ; Sugano, Yasushi ; Sugai, Takeshi. / Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin. In: Tetrahedron. 1989 ; Vol. 45, No. 17. pp. 5469-5476.
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