
%0 Journal Article
%A Cambie, RC 
%A Franich, RA 
%T Chemistry of the Podocarpaceae. XXIX. The preparation of 6-oxygenated derivatives of Abieta-8,11,13-trien-18-oic acid
%J Australian Journal of Chemistry
%D 1971/03/01
%V 24
%N 3
%P 571-582
%K 
%R https://doi.org/10.1071/CH9710571
%U https://www.publish.csiro.au/paper/CH9710571 
%X     Peracid oxidation of the enol acetate (23) derived from the C 7 ketone (6) provides a method for introducing an oxygenated substituent into the C 6 position of abieta-8,11,13-trien-18-oic acid (1). Reduction of the keto acetate (10) with sodium borohydride and hydrogenolysis of the C 7 hydroxy group of the hydroxy acetate (28) affords the 6-acetate (33) in 55% overall yield from methyl abieta- 8,11,13-trien-18-oate (2). Hydrolysis of the acetoxy ester (33) followed by re-methylation of the C 4 carboxy group and oxidation of the hydroxy ester (34) gives the C 6 ketone (35). 
