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

Hiromichi Ohta; Yoichi Kimura; Yasushi Sugano; Takeshi Sugai

doi:10.1016/S0040-4020(01)89493-X

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

Hiromichi Ohta, Yoichi Kimura, Yasushi Sugano, Takeshi Sugai

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

59 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 language	English
Pages (from-to)	5469-5476
Number of pages	8
Journal	Tetrahedron
Volume	45
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4020(01)89493-X
Publication status	Published - 1989

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4020(01)89493-X

Fingerprint Dive into the research topics of 'Enzymatic kinetic resolution of cyanohydrin acetates and its application to the synthesis of (S)-(-)-frontalin'. Together they form a unique fingerprint.

Cite this

@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 -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this