Access to Wieland-Miescher ketone in an enantiomerically pure form by a kinetic resolution with yeast-mediated reduction

Ken Ichi Fuhshuku, Nobutaka Funa, Tomohiro Akeboshi, Hiromichi Ohta, Hiroyuki Hosomi, Shigeru Ohba, Takeshi Sugai

研究成果: Article

44 引用 (Scopus)

抄録

Both enantiomers of Wieland-Miescher ketone [3,4,8,8a-tetrahydro-8a- methyl-1,6(2H, 7H)-naphthalenedione], in a highly enantiomerically enriched form, became readily available by a newly developed kinetic resolution with yeast-mediated reduction. From a screening of yeast strains, Torulaspora delbrueckii IFO 10921 was selected. The collected cells of this strain, obtained by an incubation in a glucose medium, smoothly reduced only the isolated carbonyl group of the (S)enantiomer, while the (R)-enantiomer remained intact. Starting from both enantiomers (~70% ee) prepared by an established proline-mediated asymmetric Robinson annulation, the reduction with T. delbrueckii gave the (R)-enantiomer (98% ee) and the corresponding alcohol (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methyl-2(3H)- naphthalenone (94% ee, 94% de) in preparative scale in nearly quantitative yields. An approach for the asymmetric synthesis of the Wieland-Miescher ketone was also successful. 2-Methyl-2-(3-oxobutyl)-1,3-cyclohexanedione, the prochiral precursor, was reduced with this strain to give a cyclic acetal form of (2S,3S)-3-hydroxy-2-methyl-2-(3-oxobutyl)cyclohexanone, in a stereomerically pure form.

元の言語English
ページ(範囲)129-135
ページ数7
ジャーナルJournal of Organic Chemistry
65
発行部数1
DOI
出版物ステータスPublished - 2000 1 14

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Enantiomers
Ketones
Yeast
Kinetics
Naphthoquinones
Acetals
Proline
Screening
Alcohols
Glucose

ASJC Scopus subject areas

  • Organic Chemistry

これを引用

Access to Wieland-Miescher ketone in an enantiomerically pure form by a kinetic resolution with yeast-mediated reduction. / Fuhshuku, Ken Ichi; Funa, Nobutaka; Akeboshi, Tomohiro; Ohta, Hiromichi; Hosomi, Hiroyuki; Ohba, Shigeru; Sugai, Takeshi.

:: Journal of Organic Chemistry, 巻 65, 番号 1, 14.01.2000, p. 129-135.

研究成果: Article

Fuhshuku, Ken Ichi ; Funa, Nobutaka ; Akeboshi, Tomohiro ; Ohta, Hiromichi ; Hosomi, Hiroyuki ; Ohba, Shigeru ; Sugai, Takeshi. / Access to Wieland-Miescher ketone in an enantiomerically pure form by a kinetic resolution with yeast-mediated reduction. :: Journal of Organic Chemistry. 2000 ; 巻 65, 番号 1. pp. 129-135.
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abstract = "Both enantiomers of Wieland-Miescher ketone [3,4,8,8a-tetrahydro-8a- methyl-1,6(2H, 7H)-naphthalenedione], in a highly enantiomerically enriched form, became readily available by a newly developed kinetic resolution with yeast-mediated reduction. From a screening of yeast strains, Torulaspora delbrueckii IFO 10921 was selected. The collected cells of this strain, obtained by an incubation in a glucose medium, smoothly reduced only the isolated carbonyl group of the (S)enantiomer, while the (R)-enantiomer remained intact. Starting from both enantiomers (~70{\%} ee) prepared by an established proline-mediated asymmetric Robinson annulation, the reduction with T. delbrueckii gave the (R)-enantiomer (98{\%} ee) and the corresponding alcohol (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methyl-2(3H)- naphthalenone (94{\%} ee, 94{\%} de) in preparative scale in nearly quantitative yields. An approach for the asymmetric synthesis of the Wieland-Miescher ketone was also successful. 2-Methyl-2-(3-oxobutyl)-1,3-cyclohexanedione, the prochiral precursor, was reduced with this strain to give a cyclic acetal form of (2S,3S)-3-hydroxy-2-methyl-2-(3-oxobutyl)cyclohexanone, in a stereomerically pure form.",
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AU - Fuhshuku, Ken Ichi

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AU - Akeboshi, Tomohiro

AU - Ohta, Hiromichi

AU - Hosomi, Hiroyuki

AU - Ohba, Shigeru

AU - Sugai, Takeshi

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N2 - Both enantiomers of Wieland-Miescher ketone [3,4,8,8a-tetrahydro-8a- methyl-1,6(2H, 7H)-naphthalenedione], in a highly enantiomerically enriched form, became readily available by a newly developed kinetic resolution with yeast-mediated reduction. From a screening of yeast strains, Torulaspora delbrueckii IFO 10921 was selected. The collected cells of this strain, obtained by an incubation in a glucose medium, smoothly reduced only the isolated carbonyl group of the (S)enantiomer, while the (R)-enantiomer remained intact. Starting from both enantiomers (~70% ee) prepared by an established proline-mediated asymmetric Robinson annulation, the reduction with T. delbrueckii gave the (R)-enantiomer (98% ee) and the corresponding alcohol (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methyl-2(3H)- naphthalenone (94% ee, 94% de) in preparative scale in nearly quantitative yields. An approach for the asymmetric synthesis of the Wieland-Miescher ketone was also successful. 2-Methyl-2-(3-oxobutyl)-1,3-cyclohexanedione, the prochiral precursor, was reduced with this strain to give a cyclic acetal form of (2S,3S)-3-hydroxy-2-methyl-2-(3-oxobutyl)cyclohexanone, in a stereomerically pure form.

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