Incorporation of anthranilate-d 4 into DIMBOA in maize

P Kumar, WS Chilton

Index: Kumar, Praveen; Chilton, William Scott Tetrahedron Letters, 1994 , vol. 35, # 20 p. 3247 - 3250

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Citation Number: 9

Abstract

Abstract 2, 4-Dihydroxy-7-methoxy-2H-1, 4-benzoxazin-3 (4H)-one (DIMBOA) is synthesized in maize from anthranilic acid-d 4 with high retention of deuterium. Retention of deuterium is only consistent with a mechanism of oxidative decarboxylation of o-carboxyanilinoribulose-5- phosphate or other anthranilate derivative via an intermediate in which oxygenation occurs at the carboxyl-bearing ortho carbon before decarboxylation.