
%0 Journal Article
%A Cameron, DW 
%A Deutscher, KR 
%A Feutrill, GI 
%T Nucleophilic alkenes. IX. Addition of 1,1-dimethoxyethene to azanaphthoquinones: synthesis of bostrycoidin and 8-O-methylbostrycoidin
%J Australian Journal of Chemistry
%D 1982/07/01
%V 35
%N 7
%P 1439-1450
%K 
%R https://doi.org/10.1071/CH9821439
%U https://www.publish.csiro.au/paper/CH9821439 
%X Reaction of 1,1-dimethoxyethene with azanaphthoquinones leads to pairs of isomeric dimethoxy-azaanthraquinones by means of 1:2-addition. A photochemical procedure has been developed for substituting these dimethoxy products by a further methoxy, amino or a hydroxy group peri to carbonyl. In this way the antibiotic bostrycoidin (1) and its 8-O-methyl derivative (2), the only natural 2-azaanthraquinones, have been synthesized for the first time. 
