A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor

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-ornith...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-05, Vol.67 (11), p.3595-3600
Main Authors: Qian, Xinhua, Zheng, Bin, Burke, Brian, Saindane, Manohar T, Kronenthal, David R
Format: Article
Language:English
Subjects:
Anti-Asthmatic Agents - chemical synthesis
Azetidines - chemical synthesis
Azetidines - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Ornithine - chemistry
Piperazines - chemical synthesis
Preparations and properties
Serine Endopeptidases - metabolism
Serine Proteinase Inhibitors - chemical synthesis
Stereoisomerism
Tryptases
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010757o