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

薬科学科

研究成果: Article › 査読

60 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	5469-5476
ページ数	8
ジャーナル	Tetrahedron
巻	45
号	17
DOI	https://doi.org/10.1016/S0040-4020(01)89493-X
出版ステータス	Published - 1989

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/S0040-4020(01)89493-X

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author = "Hiromichi Ohta and Yoichi Kimura and Yasushi Sugano and Takeshi Sugai",

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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.

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JF - Tetrahedron

SN - 0040-4020

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

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