Document Type
Dissertation
Date of Award
1979
Abstract
Our interest in the conversion of a resin acid to a C-aryl-18-nor-steroid was to see if this class of compounds could compete as starting materials in the medicinal chemistry field. Since resin acid derivatives are rather inexpensive compared to steroid systems, the economics seemed attractive.In order to cyclize a ring D onto the resin acid skeleton, it was important to convert the isopropyl group to an acetyl group. To achieve this goal, the Tahara modification of the Sanderson oxidation of dehydroabietonitrile was applied, to yield the 7-oxo-13-acetyl dehydroabietonitrile and the 7-oxo-13-isopropenyl derivative.Treating the diketone with formaldehyde and dimethylamine hydro-chloride, yielded the Mannich base, which with methyl-iodide formed the methiodide salt plus the vinyl-phenyl-ketone derivative.Cyclization of the vinyl product by means of a melt of aluminum chloride sodium chloride gave the desired steroid as the sole product.
Recommended Citation
Gawish, Ali Abd El-Salam, "The Synthesis of C-aryl-18-nor-steroids From Resin Acids and Their Derivatives." (1979). All ETDs from UAB. 7088.
https://digitalcommons.library.uab.edu/etd-collection/7088
Comments
PhD - ProQuest publication number 8028373