
TY  - JOUR
A1  - Cossey, AL 
A1  - Mander, LN 
A1  - Turner, JV 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 9
SP  - 2061
EP  - 2069
KW  - 
UR  - https://doi.org/10.1071/CH9802061 
N2  - (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. 
ER  -

