
TY  - JOUR
A1  - Bennett, CR 
A1  - Cambie, RC 
A1  - Fullerton, TJ 
T1  - Chemistry of the Podocarpaceae. XVII. Ring-A modifications of O-methylpodocarpic acid
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1968
VL  - 21
IS  - 10
SP  - 2473
EP  - 2482
KW  - 
UR  - https://doi.org/10.1071/CH9682473 
N2  - 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. 
ER  -

