
TY  - JOUR
A1  - Cambie, RC 
A1  - Joblin, KN 
A1  - Preston, AF 
T1  - Chemistry of the Podocarpaceae. XXXIV. Some oxidation products of (13R)-Labda-8(17),14-dien-13-ol (Manool)
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1971
VL  - 24
IS  - 11
SP  - 2365
EP  - 2377
KW  - 
UR  - https://doi.org/10.1071/CH9712365 
N2  - Some products from the oxidation of manool (3) are examined. Potassium permanganate gives, inter alia, the hitherto unreported compound (16) while sodium dichromate gives the methyl ketone (5) and, as the major product, a mixture of (Z)- and (E)-&#945;,&#946;-unsaturated aldehydes (21). Hypoiodite oxidation of the methyl ketone (5) gives the &#945;-hydroxy acid (26) in addition to the expected acid (6). Products of nucleophilic substitution have also been obtained from the hypoiodite oxidation of the methyl ketones (9) and (37). Peracid oxidation of the methyl ketone (5) gives the epoxy acetate (41) which, on reduction with lithium aluminium hydride, affords the diol (7), from which the odoriferous oxide (30) can be prepared. Oxidations leading to formation of the dione (10) are investigated. 
ER  -

