
TY  - JOUR
A1  - Cambie, RC 
A1  - Denny, WA 
T1  - Chemistry of the Podocarpaceae. XXIII. Preparation and reactions of some lactone derivatives of 12-Methoxypodocarpa-8,11,13-trien-19-oic acid
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1969
VL  - 22
IS  - 9
SP  - 1989
EP  - 2000
KW  - 
UR  - https://doi.org/10.1071/CH9691989 
N2  - The parent lactone (V) of a series of 12-methoxypodocarpa-8,11,13- trien-19-oic acid derivatives has been prepared by successive dehydration and hydrogenation of the 7&#945;- and 7&#946;-hydroxy lactones (VII) and (VIII), and also by reduction of the 7-keto lactone (IV) with diborane. Attack by nucleophiles on the 7&#946;-hydroxy lactone (VIII) is a convenient method for the preparation of less readily available 7&#945;- substituted lactones. Treatment of the 7-keto lactone (IV) with sodium hydroxide in methanol effects a fragmentation reaction to give the diosphenol (XXIV), providing a potential method for the formation of hitherto inaccessible 6,7-diketones with a trans-fused A/B ring junction. Treatment of the diosphenol (XXV) with potassium hydroxide affords the cis-fused A/B ring junction diketo acid (XXXI) rather than the product of an expected benzilic acid rearrangement. 
ER  -

