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

58 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

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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.",

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AU - Kimura, Yoichi

AU - Sugano, Yasushi

AU - Sugai, Takeshi

PY - 1989

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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.

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