Piatak, David M.||Kevill, Dennis N.
M.S. (Master of Science)
Department of Chemistry
Smilagenin; Steroids; Mevalonic acid
2-Â¹â�´C-Mevalonic acid was converted to smilagenin in an Agave lecheguilla plant. The sapogenin was isolated by extraction and separated by thin layer and paper chromatographic processes. Its presence was established by dilution with carrier smilagenin and recrystallization to constant specific activity. The material was also converted to smilagenin acetate (with acetic anhydride-pyridine) and to smilagenone by hydrolysis then oxidation of the acetate. Both derivatives were recrystallized to constant specific activity. These results fully established the conversion of mevalonic acid to smilagenin in this plant. In part B, the use of ruthenium tetroxide for degrading aromatic steroids has been explored. 3,17Î²-Dipropionylosyestra-1,3,5(10)- triene; 4-bromo-3,17Î²-diacetoxyestra-1,3,5(10)-triene; 17Î²-acetoxy-3- methoxyestra-1,3,5(10)-triene; 3Î², 16Î±, 17Î²-triacetoxyestra-1,3,5(10)- triene; 3Î²-acetoxyestra-1,3,5(10)-triene-17-one; 3Î²-hydroxy-2,4-dinitroestra-1,3,5(10)-triene-17-one and 17Î²-acetoxy-l-chloro-4-methylestra-1,3,5(10)-triene were synthesized and an oxidation of each with ruthenium tetroxide was carried out. 3,17Î²-Dipropionyloxy-estra-1,3,5(10)-triene; 3Î², 16Î±, 17Î²-triacetoxyestra-1,3,5(10)-triene and 3Î²-acetoxyestra-1,3,5(10)-trien-17-one gave the corresponding 9Î±-hydroxy-6-keto products. Their structures were determined from spectroscopic data and elemental analysis. 17Î²-acetoxy-3-methoxyestra-1,3,5(10)-triene, 4-bromo-3, 17Î²-diacetoxyestra-1,3,5(10)-triene, and 17Î²-acetoxy-l-chloro-4-methylestra-1,3,5(10)-triene gave the 17-acetoxy diacid resulting from degradation of the ring A and terminating at carbons 5 and 10 as expected. 3Î²-Hydroxy-2,4-dinitroestra-1,3,5(10) trien-17-one was degraded to 3(1-oxo-8Î²-methyl-5Î²-carboxyl-trans-perhydroindanyl-4Î±) propionic acid.
Ekundayo, Olusegun, "The Conversion of 2-Â¹â�´C-mevalonic acid to smilagenin in Agave lecheguilla, and Ruthenium tetroxide oxidation of some ring A steroids" (1971). Graduate Research Theses & Dissertations. 5382.
vi, 59 pages
Northern Illinois University
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