CHIRAL SYNTHESIS OF (-8'-DEMETHYL ABSCISIC-ACID())

Authors
ROSE PA LEI B SHAW AC WALKERSIMMONS MK NAPPER S QUAIL JW AHRAMS SR
Citation
Pa. Rose et al., CHIRAL SYNTHESIS OF (-8'-DEMETHYL ABSCISIC-ACID()), Canadian journal of chemistry, 74(10), 1996, pp. 1836-1843
Citations number
27
Categorie Soggetti
Chemistry
Journal title
Canadian journal of chemistry → ACNP
ISSN journal
00084042
Volume
74
Issue
10
Year of publication
1996
Pages
1836 - 1843
Database
ISI
SICI code
0008-4042(1996)74:10<1836:CSO(A>2.0.ZU;2-M
Abstract
An enantioselective synthesis of (+)-8'-demethyl ABA (2) is described. The chiral intermediate 7 was prepared by yeast reduction of a substi tuted monoprotected cyclohexa-2,5-dien-1,4-dione (9) synthesized throu gh a phenol oxidation. The scope and limitations of the phenol oxidati on is described. 8'-Demethyl ABA shows ABA-like activity in wheat embr yo germination inhibition, showing that the 8'-methyl group is not ess ential for biological activity.