
%0 Journal Article
%A Cossey, AL 
%A Mander, LN 
%A Turner, JV 
%T Synthetic plant growth regulators. VI. The partial synthesis of optically active (4&#946;,15&#945;)-18-Norkaurene-15-carboxylic acids from (4&#946;)-18-norkauren-3-one by means of a pyrrolidinium ylide rearrangement
%J Australian Journal of Chemistry
%D 1980/09/01
%V 33
%N 9
%P 2061-2069
%K 
%R https://doi.org/10.1071/CH9802061
%U https://www.publish.csiro.au/paper/CH9802061 
%X (4&#946;)-18-Norkaur-16-en-3-one (4a) was alternatively acetalized (ethanediol/Dowex resin) or deoxygenated (tosylhydrazine/sodium borohydride); allylic bromination (N-bromosuccinimide) of the products, followed by alkylation of pyrrolidine gave primary allylic amines which were quaternized with chloroacetonitrile. Potassium t-butoxide-induced [2,3]-sigmatropic rearrangement, followed by acidic hydrolysis and Jones oxidation, gave respectively (4&#946;,15&#945;)-3-oxo-18-norkaur-16-ene-15- carboxylic acid (10a) and (4&#946;,15&#945;)-18-norkaur-16-ene-15-carboxylic acid. Reductions of (4a) and (10a) gave, with K-Selectride, axial (3&#946;)- alcohols and, with sodium borohydride, mainly equatorial (3&#945;)-alcohols. Details of a related conversion of (+)-phyllocladene into (15&#945;)- phyllocladene-15-carboxylic acid are also recorded. 
