
%0 Journal Article
%A Cambie, C. 
%A Denny, William A. 
%A Hay, Michael P. 
%A Mitchell, Lorna H. 
%A Rutledge, Peter S. 
%A Woodgate, Paul D. 
%T Modifications of Rings B and C of Podocarpic Acid: Towards the Synthesis of Quassinoids Richard
%J Australian Journal of Chemistry
%D 1998/12/24
%V 52
%N 1
%P 7-18
%K 
%R https://doi.org/10.1071/C98015
%U https://www.publish.csiro.au/paper/C98015 
%X Attempts to alkylate products from Birch reductions of derivatives of podocarpic acid are reported. Attempted reductive silylation of ring C of methyl 12-methoxypodocarpa-8,11,13-trien-19-oate (5) gives products of C4 ester reduction only. The enantiopure form of the bis(ethylene acetal) (15) of 19-norpodocarp-8-ene-3,12-dione, a potentially useful intermediate for quassinoid synthesis, has been prepared from the ketone (34). Functionality at C8 on the &#946;-face has been successfully introduced by abnormal Reimer&#8211;Tiemann reactions of podocarpic acid (2) and its 13-methyl derivative (10). The saturated ketone (48) has been converted into an &#945;,&#946;-unsaturated ketone (18) which has potential for introducing functionality at C14. 
