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

Authors
Kiyota, H Nakabayashi, M Oritani, T
Citation
H. Kiyota et al., 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, TETRAHEDR-A, 10(19), 1999, pp. 3811-3817
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
19
Year of publication
1999
Pages
3811 - 3817
Database
ISI
SICI code
0957-4166(19990924)10:19<3811:HPO(A(>2.0.ZU;2-T
Abstract
Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2-cyclohex en-1-one (phorenol), which are versatile synthetic intermediates for abscis ic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Naga se) enriched the (S)-ester, while lipase P (Amano) afforded the (R)-ester. (C) 1999 Elsevier Science Ltd. All rights reserved.