Preparation of Optically Active α-Hydroxy Acid Derivatives by Microbial Hydrolysis of Cyanohydrins and Its Application to the Synthesis of (R)-4-Dodecanolide†

Hideaki Kakeya; Naoko Sakai; Takeshi Sugai; Hiromichi Ohta

doi:10.1271/bbb1961.55.1877

Preparation of Optically Active α-Hydroxy Acid Derivatives by Microbial Hydrolysis of Cyanohydrins and Its Application to the Synthesis of (R)-4-Dodecanolide^†

Hideaki Kakeya, Naoko Sakai, Takeshi Sugai, Hiromichi Ohta

School of Pharmaceutical Sciences

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

1 Citation (Scopus)

Abstract

Both enantiomers of aliphatic and aromatic cyanohydrins were hydrolyzed with the aid of Rhodococcus butanica ATCC 21197 to afford optically active α-hydroxy acids. The usefulness of this reaction is demonstrated by the synthesis of optically pure (R)-4-dodecanolide, a defensive secretion of rove beetles, starting from (R)-2-hydroxydecanenitrile.

Original language	English
Pages (from-to)	1877-1881
Number of pages	5
Journal	Agricultural and biological chemistry
Volume	55
Issue number	7
DOIs	https://doi.org/10.1271/bbb1961.55.1877
Publication status	Published - 1991

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)
Agricultural and Biological Sciences(all)

Access to Document

10.1271/bbb1961.55.1877

Cite this

@article{b51ddd8b988b45abb408054f7d0531f0,

title = "Preparation of Optically Active α-Hydroxy Acid Derivatives by Microbial Hydrolysis of Cyanohydrins and Its Application to the Synthesis of (R)-4-Dodecanolide†",

abstract = "Both enantiomers of aliphatic and aromatic cyanohydrins were hydrolyzed with the aid of Rhodococcus butanica ATCC 21197 to afford optically active α-hydroxy acids. The usefulness of this reaction is demonstrated by the synthesis of optically pure (R)-4-dodecanolide, a defensive secretion of rove beetles, starting from (R)-2-hydroxydecanenitrile.",

author = "Hideaki Kakeya and Naoko Sakai and Takeshi Sugai and Hiromichi Ohta",

year = "1991",

doi = "10.1271/bbb1961.55.1877",

language = "English",

volume = "55",

pages = "1877--1881",

journal = "Bioscience, Biotechnology and Biochemistry",

issn = "0916-8451",

publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",

number = "7",

}

TY - JOUR

T1 - Preparation of Optically Active α-Hydroxy Acid Derivatives by Microbial Hydrolysis of Cyanohydrins and Its Application to the Synthesis of (R)-4-Dodecanolide†

AU - Kakeya, Hideaki

AU - Sakai, Naoko

AU - Sugai, Takeshi

AU - Ohta, Hiromichi

PY - 1991

Y1 - 1991

N2 - Both enantiomers of aliphatic and aromatic cyanohydrins were hydrolyzed with the aid of Rhodococcus butanica ATCC 21197 to afford optically active α-hydroxy acids. The usefulness of this reaction is demonstrated by the synthesis of optically pure (R)-4-dodecanolide, a defensive secretion of rove beetles, starting from (R)-2-hydroxydecanenitrile.

AB - Both enantiomers of aliphatic and aromatic cyanohydrins were hydrolyzed with the aid of Rhodococcus butanica ATCC 21197 to afford optically active α-hydroxy acids. The usefulness of this reaction is demonstrated by the synthesis of optically pure (R)-4-dodecanolide, a defensive secretion of rove beetles, starting from (R)-2-hydroxydecanenitrile.

UR - http://www.scopus.com/inward/record.url?scp=85007676916&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85007676916&partnerID=8YFLogxK

U2 - 10.1271/bbb1961.55.1877

DO - 10.1271/bbb1961.55.1877

M3 - Article

AN - SCOPUS:85007676916

SN - 0916-8451

VL - 55

SP - 1877

EP - 1881

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 7

ER -

Preparation of Optically Active α-Hydroxy Acid Derivatives by Microbial Hydrolysis of Cyanohydrins and Its Application to the Synthesis of (R)-4-Dodecanolide^†

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this