Journal
MOLECULES
Volume 24, Issue 11, Pages -Publisher
MDPI
DOI: 10.3390/molecules24112081
Keywords
deuterated fatty acids; epoxides; hydroxy fatty acids; -lactones; organocatalysis
Funding
- Special Account for Research Grants of the National and Kapodistrian University of Athens [13300]
- Supporting Post-Doctoral Researchers Action of the Operational Programme Human Resources Development, Education and Lifelong Learning with priority axes 6,8,9
- European Social Fund (ESF)
- Greek National Resources
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3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan's third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty -lactones, corresponding to 4-hydroxy fatty acids, was also explored.
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