
%0 Journal Article
%A Cambie, RC 
%A Higgs, PI 
%A Rutledge, PS 
%A Woodgate, PD 
%T Aryne Chemistry of Podocarpic Acid Derivatives
%J Australian Journal of Chemistry
%D 1994/08/01
%V 47
%N 8
%P 1483-1508
%K 
%R https://doi.org/10.1071/CH9941483
%U https://www.publish.csiro.au/paper/CH9941483 
%X The anthranilic acid (2), a key intermediate for the generation of an aryne at C13 of podocarpic acid derivatives, was synthesized from the 14-amino compound (5) which in turn was generated regiospecifically in high yield by treatment of the 13-bromo compound (25) with sodamide in liquid ammonia. The amine was converted into the anthranilic acid by two separate routes: firstly by directed lithiation and trapping of the lithium species with a CO2 moiety, and secondly by oxidative cleavage of an isatin fused across positions 13 and 14. 
