Abstract
A highly stereoselective synthesis of the novel tryptase inhibitor BMS-262084 was developed. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans-azetidinone 13. BMS-262084 was prepared in 10 steps from D-ornithine in 30% overall yield.
MeSH terms
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Anti-Asthmatic Agents / chemical synthesis
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Azetidines / chemical synthesis*
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Azetidines / chemistry*
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Ornithine / chemistry
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Piperazines / chemical synthesis*
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Serine Endopeptidases / metabolism
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Serine Proteinase Inhibitors / chemical synthesis*
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Stereoisomerism
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Tryptases
Substances
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2-azetidinone
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Anti-Asthmatic Agents
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Azetidines
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BMS-262084
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Piperazines
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Serine Proteinase Inhibitors
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Ornithine
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Serine Endopeptidases
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Tryptases