
TY  - JOUR
A1  - Cambie, RC 
A1  - Franich, RA 
T1  - Chemistry of the Podocarpaceae. XXVII. Ring-c modifications of methyl abieta-8,11,13-trien-18-oate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1971
VL  - 24
IS  - 1
SP  - 117
EP  - 134
KW  - 
UR  - https://doi.org/10.1071/CH9710117 
N2  - Functionalization of the isopropyl group of methyl abieta-8,11,13- trien-18-oate (8) has been achieved by intramolecular cyclizations of the 12-carboxy derivative (10) with lead tetraacetate and by thermolysis of the diazomethyl ketone (11).     Nitration of methyl 12-acetylabieta-8,11,13-trien-18-oate (9) has given the products (21) and (30), arising from nitrodeacylation and nitrodealkylation reactions, respectively. The nitro ketone (30) has been converted into methyl 13-hydroxypodocarpa-8,11,13-trien-18-oate (38) in 26% overall yield from the ester (8). Birch reduction of the methyl ether of the phenol (38) afforded the enone (50), a potentially useful intermediate for synthesis. 
ER  -

