
%0 Journal Article
%A Hensens, OD 
%A Lewis, KG 
%A Tucker, DJ 
%T Reactions of primulagenin A. IV. Ring expansion in Oleana-12,15-diene-3b,28-diol and the related 13(18),15-diene isomer
%J Australian Journal of Chemistry
%D 1980/11/01
%V 33
%N 11
%P 2517-2529
%K 
%R https://doi.org/10.1071/CH9802517
%U https://www.publish.csiro.au/paper/CH9802517 
%X Treatment of oleana-12,15-diene-3&#946;,28-diol 3-acetate with a cold pyridine solution of p-toluene-sulfonyl chloride leads to expansion of ring D with the formation of 28-nor-D(16a)-homo-oleana-12,15,17(18)- trien-3&#946;-yl acetate (7). Under more vigorous conditions a mixture of the D-homo compound (7) and a double bond isomer (11) is obtained. Subjection of oleana-13(18),15-diene-3&#946;,28- diol 3-acetate to similar reflux conditions also forms the D-homo compound (7). 
