Abstract
An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric methallylation of 3-chloro-1-phenylpropan-1-one catalyzed by the highly effective organocatalyst (S)-3,3'-F2-BINOL under solvent-free and metal-free conditions.
MeSH terms
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11-beta-Hydroxysteroid Dehydrogenases / antagonists & inhibitors*
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11-beta-Hydroxysteroid Dehydrogenases / chemistry
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Catalysis
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Ketones / chemistry
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Naphthols / chemical synthesis*
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Naphthols / chemistry
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Propane / analogs & derivatives*
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Propane / chemical synthesis
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Propane / chemistry
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Stereoisomerism
Substances
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3,3'-F2-BINOL
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3-chloro-1-phenylpropan-1-one
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Ketones
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Naphthols
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11-beta-Hydroxysteroid Dehydrogenases
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Propane