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 journal › Article

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

Fingerprint

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 journal › Article

Ohta, H, Kimura, Y, Sugano, Y & Sugai, T 1989, 'Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin', Tetrahedron, vol. 45, no. 17, pp. 5469-5476. https://doi.org/10.1016/S0040-4020(01)89493-X
Ohta H, Kimura Y, Sugano Y, Sugai T. Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin. Tetrahedron. 1989;45(17):5469-5476. https://doi.org/10.1016/S0040-4020(01)89493-X
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.
@article{f5bd0a82f13a407faed9c053d2b7ce6d,
title = "Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin",
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.",
author = "Hiromichi Ohta and Yoichi Kimura and Yasushi Sugano and Takeshi Sugai",
year = "1989",
doi = "10.1016/S0040-4020(01)89493-X",
language = "English",
volume = "45",
pages = "5469--5476",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "17",

}

TY - JOUR

T1 - Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin

AU - Ohta, Hiromichi

AU - Kimura, Yoichi

AU - Sugano, Yasushi

AU - Sugai, Takeshi

PY - 1989

Y1 - 1989

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0001639775&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001639775&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)89493-X

DO - 10.1016/S0040-4020(01)89493-X

M3 - Article

AN - SCOPUS:0001639775

VL - 45

SP - 5469

EP - 5476

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 17

ER -

Access to Document