
TY  - JOUR
A1  - Cambie, C. 
A1  - Denny, William A. 
A1  - Hay, Michael P. 
A1  - Mitchell, Lorna H. 
A1  - Rutledge, Peter S. 
A1  - Woodgate, Paul D. 
T1  - Modifications of Rings B and C of Podocarpic Acid: Towards the Synthesis of Quassinoids Richard
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1998
VL  - 52
IS  - 1
SP  - 7
EP  - 18
KW  - 
UR  - https://doi.org/10.1071/C98015 
N2  - 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. 
ER  -

