Journal of natural products

A Mechanistic Dehydration Study with [2-13C]-DIMBOA

H Hao, J Sieler, D Sicker

Index: Hao, Huang; Sieler, Joachim; Sicker, Dieter Journal of Natural Products, 2002 , vol. 65, # 4 p. 466 - 469

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Citation Number: 4

Abstract

Dehydration of a 2-13C-labeled synthetic sample of the natural aglucone 2, 4-dihydroxy-7- methoxy-2 H-1, 4-benzoxazin-3 (4 H)-one ([2-13C]-DIMBOA, 10) using N- ethoxycarbonyltrichloroacetaldimine led to 3-formyl-6-methoxybenzoxazolin-2 (3 H)-one (13C-labeled FMBOA, 11) with complete transfer of the 13C label into the-CHO group. On the basis of this finding, a mechanism for the dehydration is proposed.