INCORPORATION OF ANTHRANILATE-D(4) INTO DIMBOA IN MAIZE

Authors
KUMAR P CHILTON WS
Citation
P. Kumar et Ws. Chilton, INCORPORATION OF ANTHRANILATE-D(4) INTO DIMBOA IN MAIZE, Tetrahedron letters, 35(20), 1994, pp. 3247-3250
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
20
Year of publication
1994
Pages
3247 - 3250
Database
ISI
SICI code
0040-4039(1994)35:20<3247:IOAIDI>2.0.ZU;2-9
Abstract
,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) is synthes ized in maize from anthranilic acid-dir with high retention of deuteri um. Retention of deuterium is only consistent with a mechanism of oxid ative decarboxylation of o-carboxyanilinoribulose-5-phosphate or other anthranilate derivative via an intermediate in which oxygenation occu rs at the carboxyl-bearing ortho carbon before decarboxylation.