Preparation of optically active α-hydroxy acid derivatives by microbial hydrolysis of cyanohydrins and its application to the synthesis of (R)-4-dodeeanolide

Hideaki Kakeya; Naoko Sakai; Takeshi Sugai; Hiromichi Ohta

doi:10.1080/00021369.1991.10870845

Preparation of optically active α-hydroxy acid derivatives by microbial hydrolysis of cyanohydrins and its application to the synthesis of (R)-4-dodeeanolide

Hideaki Kakeya, Naoko Sakai, Takeshi Sugai, Hiromichi Ohta

School of Pharmaceutical Sciences

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

32 Citations (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/10.1080/00021369.1991.10870845
Publication status	Published - 1991 Jul

ASJC Scopus subject areas

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

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10.1080/00021369.1991.10870845

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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.",

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AU - Sugai, Takeshi

AU - Ohta, Hiromichi

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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.

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Preparation of optically active α-hydroxy acid derivatives by microbial hydrolysis of cyanohydrins and its application to the synthesis of (R)-4-dodeeanolide

Abstract

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