
%0 Journal Article
%A Bennett, CR 
%A Cambie, RC 
%A Fullerton, TJ 
%T Chemistry of the Podocarpaceae. XVII. Ring-A modifications of O-methylpodocarpic acid
%J Australian Journal of Chemistry
%D 1968/10/01
%V 21
%N 10
%P 2473-2482
%K 
%R https://doi.org/10.1071/CH9682473
%U https://www.publish.csiro.au/paper/CH9682473 
%X Methods for the conversion of 0-methylpodocarpic acid (I) into 12-methoxy-16-norpodocarpa-8,11,13-trien-4-amine (11) have been examined, a Curtius reaction on the acid chloride (IV) followed by hydrolysis of the isocyanate (111) with 85% w/w sulphuric acid affording the highest overall yield (44%). Some &quot;simple deaminations&quot; involving no change in oxidation state, have been investigated as possible routes to alkenes suitable for further modification of the A ring of podocarpio acid. These include nitrous acid deamination, treatment of the N-benzoate (VIII) with phosphorus pentabromide or pentachloride, and pyrolysis of the tertiary amine oxide (VII) or quaternary methylammonium iodide. 
