Abstract
Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Amides / chemical synthesis*
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Amides / chemistry
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Bimatoprost
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Cloprostenol / analogs & derivatives*
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Cloprostenol / chemical synthesis
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Cloprostenol / chemistry
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Dinoprost / analogs & derivatives
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Dinoprost / chemical synthesis*
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Dinoprost / chemistry
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Latanoprost
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Molecular Structure
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Prostaglandins F, Synthetic / chemical synthesis*
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Prostaglandins F, Synthetic / chemistry
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Prostaglandins, Synthetic / chemical synthesis*
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Prostaglandins, Synthetic / chemistry
Substances
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Aldehydes
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Amides
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Prostaglandins F, Synthetic
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Prostaglandins, Synthetic
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Cloprostenol
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Latanoprost
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3-hydroxybutanal
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Dinoprost
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Bimatoprost