
TY  - JOUR
A1  - Cambie, RC 
A1  - Hayward, RC 
A1  - Palmer, BD 
A1  - Robertson, JD 
A1  - Rutledge, PS 
A1  - Woodgate, PD 
T1  - Chemistry of the Podocarpaceae. LXIV. Studies in the ambergris odorant field
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1982
VL  - 35
IS  - 8
SP  - 1699
EP  - 1707
KW  - 
UR  - https://doi.org/10.1071/CH9821699 
N2  - The cyclic ethers 17-nor-16-oxa-l3&#946;-kaurane (8) and 15,16-epoxy-17-nor-15,16-seco-8&#946;,13&#946;-kaurane (11) have been prepared from 13 &#946;-kaur-15-ene ('isophyllocladene')(1) and 13 &#946;-kaur-16-ene ('phyllocladene') (2), respectively. The derivative (8), but not (11), possesses an ambergris-type odour. Preparation of the 8 &#946;,12-epoxides (30),(31),(33) and (34) from 12-hydroxypodocarpa-8,11,13-trien-19-oic acid ('podocarpic acid') (3) indicates that substitution of the 4&#946;-methyl group destroys their potentially odoriferous nature. An attempt to prepare epimers of the C8 demethyl analogue of the known ambergris-type odorant (45) is reported; a mixture of the C13 epimers of (45) is readily prepared from the unsaturated ketone (41). 
ER  -

