Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

Hiromasa Kiyota; Miho Nakabayashi; Takayuki Oritani

doi:10.1016/S0957-4166(99)00391-2

Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

Hiromasa Kiyota, Miho Nakabayashi, Takayuki Oritani

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

14 Citations (Scopus)

Abstract

Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2- cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Nagase) enriched the (S)-ester, while lipase P (Amano) afforded the (R)- ester.

Original language	English
Pages (from-to)	3811-3817
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	10
Issue number	19
DOIs	https://doi.org/10.1016/S0957-4166(99)00391-2
Publication status	Published - Sept 24 1999
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid",

abstract = "Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2- cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Nagase) enriched the (S)-ester, while lipase P (Amano) afforded the (R)- ester.",

author = "Hiromasa Kiyota and Miho Nakabayashi and Takayuki Oritani",

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T1 - Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

AU - Kiyota, Hiromasa

AU - Nakabayashi, Miho

AU - Oritani, Takayuki

PY - 1999/9/24

Y1 - 1999/9/24

N2 - Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2- cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Nagase) enriched the (S)-ester, while lipase P (Amano) afforded the (R)- ester.

AB - Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2- cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Nagase) enriched the (S)-ester, while lipase P (Amano) afforded the (R)- ester.

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JO - Tetrahedron Asymmetry

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ER -

Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

Abstract

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