Abstract
( S)-3-Amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (OV329, 1) is being developed for the treatment of epilepsy and addiction. The previous 14-step synthesis of OV329 was low yielding, involved an unselective α-elimination to form the cyclopentene, required the use of tert-butyllithium, and produced toxic selenium byproducts in the penultimate step. A new synthesis, which avoids the aforementioned issues, was carried out on large scale, reducing the step count from 14 to 9 steps and increasing the overall yield from 3.7% to 8.1%.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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4-Aminobutyrate Transaminase / antagonists & inhibitors*
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Cyclopentanes / chemistry*
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Enzyme Inhibitors / chemical synthesis*
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Molecular Structure
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Organometallic Compounds / chemistry
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Phenylacetates / chemistry
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Selenium Compounds / chemistry
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Stereoisomerism
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Structure-Activity Relationship
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Transaminases / antagonists & inhibitors*
Substances
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Cyclopentanes
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Enzyme Inhibitors
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Organometallic Compounds
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Phenylacetates
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Selenium Compounds
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butyllithium
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cyclodrine
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Transaminases
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4-Aminobutyrate Transaminase