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 journalArticle

13 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 languageEnglish
Pages (from-to)3811-3817
Number of pages7
JournalTetrahedron Asymmetry
Volume10
Issue number19
DOIs
Publication statusPublished - Sep 24 1999
Externally publishedYes

Fingerprint

abscisic acid
Hydrolases
Abscisic Acid
hydrolysis
esters
Hydrolysis
Esters
Acetylglucosaminidase
carotenoids
preparation
Acids
Enantiomers
enantiomers
Lipases
Esterases
Carotenoids
Lipase
2-cyclohexen-1-one

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

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. / Kiyota, Hiromasa; Nakabayashi, Miho; Oritani, Takayuki.

In: Tetrahedron Asymmetry, Vol. 10, No. 19, 24.09.1999, p. 3811-3817.

Research output: Contribution to journalArticle

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