Abstract
An original, effective approach to the synthesis of natural and synthetic 5Z,9Z-dienoic acids in high yields (61-67%) and with high selectivity (>98%) was developed. The approach is based on the use of the new intermolecular catalytic cross cyclomagnesiation of terminal aliphatic and oxygenated 1,2-dienes upon treatment with Grignard reagents in the presence of the Cp2TiCl2 catalyst. High activity of (5Z,9Z)-5,9-eicosadienoic acid as a human topoisomerase I inhibitor at concentrations above 0.1 μM was elucidated.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkadienes / chemistry
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Catalysis
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DNA Topoisomerases, Type I / metabolism
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Fatty Acids, Unsaturated / chemical synthesis
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Fatty Acids, Unsaturated / chemistry*
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Fatty Acids, Unsaturated / pharmacology*
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Humans
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Topoisomerase I Inhibitors / chemical synthesis
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Topoisomerase I Inhibitors / chemistry*
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Topoisomerase I Inhibitors / pharmacology*
Substances
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5,9-eicosadienoic acid
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Alkadienes
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Fatty Acids, Unsaturated
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Topoisomerase I Inhibitors
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DNA Topoisomerases, Type I