Journal
STEROIDS
Volume 151, Issue -, Pages -Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2019.108449
Keywords
Regioselective oxidation; Cytochrome P450; Steroids; Irritable bowel syndrome; Oxysterols
Funding
- University of Texas at San Antonio (UTSA)
- Max and Minnie Tomerlin Voelcker Fund
- MAX AND MINNIE TOMERLIN VOELKCER FUND
- National Science Foundation Major Research Instrumentation grant [1625963]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1625963] Funding Source: National Science Foundation
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7 alpha-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7 alpha-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 881 or CYP8B1), the oxysterol 12 alpha-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature of this synthesis involves a regioselective C3-allylic oxidation of a 3desoxy-Delta(4)-7 alpha-formate steroid precursor to form 7 alpha-formyloxy-cholest-4-en-3-one, which was saponified to yield 7 alpha-hydroxy-cholest-4-en-3-one.
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