Abstract
A scalable synthesis of a potent renin inhibitor (1) is described. The absolute stereochemistry is set via an unprecedented diastereoselective Dieckmann cyclization directed by a remote chiral protecting group. This transformation enables preparation of chiral 1,3-[3.3.1]-diazabicyclononenes by desymmetrization of alkyl-esters, with selectivities ranging from 4 to 17:1.
MeSH terms
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Azo Compounds / chemical synthesis*
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Azo Compounds / chemistry
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Crystallography, X-Ray
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Cyclization
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Molecular Conformation
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Molecular Structure
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Protease Inhibitors / chemical synthesis*
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Protease Inhibitors / chemistry
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Protease Inhibitors / pharmacology*
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Renin / antagonists & inhibitors*
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Stereoisomerism
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Toluene / analogs & derivatives*
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Toluene / chemical synthesis
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Toluene / chemistry
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Toluene / pharmacology
Substances
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Azo Compounds
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Bridged Bicyclo Compounds, Heterocyclic
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MK-8141
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Protease Inhibitors
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Toluene
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Renin