3$\beta$-Hydroxy-cholest-5-en-7-one (15) has been reported to lower 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase activity in both mouse liver cells and whole animals. In experiments with rats, studies have shown that 15 is rapidly metabolized and excreted from the body. We synthesized 3$\beta$-hydroxy-25,26,26,26,27,27,27-heptafluorocholest-5-en-7-one (19) with the hope that blocking the sidechain metabolism at C-25 and C26 would allow sufficient quantities to accumulate in vivo and possibly lower serum cholesterol levels. 19 was synthesized via 25,26,26,26,27,27,27-heptafluorocholest-5-en-3$\beta$-ol (3) by employing the reagents chromic anhydride and 3,5-dimethylpyrazole (DMP) in methylene chloride (66% yield; $>$99% pure by NMR). A thorough characterization of 19 and its nonfluorinated counterpart 15 is presented. Several byproducts from the synthesis of 3 and 19 were discovered. Their preliminary characterizations are also reported.
Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/14040 |
Date | January 1996 |
Creators | Carroll, Jeffery Neal |
Source Sets | Rice University |
Language | English |
Detected Language | English |
Type | Thesis, Text |
Format | application/pdf |
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