
%0 Journal Article
%A Cambie, RC 
%A Denny, WA 
%T Chemistry of the Podocarpaceae. XXIII. Preparation and reactions of some lactone derivatives of 12-Methoxypodocarpa-8,11,13-trien-19-oic acid
%J Australian Journal of Chemistry
%D 1969/09/01
%V 22
%N 9
%P 1989-2000
%K 
%R https://doi.org/10.1071/CH9691989
%U https://www.publish.csiro.au/paper/CH9691989 
%X 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. 
