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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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| Published in: | Journal of organic chemistry 2002-05, Vol.67 (11), p.3595-3600 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a379t-d0336209de025574fce6a7675635ae62e62fbee2422b4d4142a6d923f34e13273 |
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| cites | cdi_FETCH-LOGICAL-a379t-d0336209de025574fce6a7675635ae62e62fbee2422b4d4142a6d923f34e13273 |
| container_end_page | 3600 |
| container_issue | 11 |
| container_start_page | 3595 |
| container_title | Journal of organic chemistry |
| container_volume | 67 |
| creator | Qian, Xinhua Zheng, Bin Burke, Brian Saindane, Manohar T Kronenthal, David R |
| description | 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. |
| doi_str_mv | 10.1021/jo010757o |
| format | article |
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Org. Chem</addtitle><date>2002-05-31</date><risdate>2002</risdate><volume>67</volume><issue>11</issue><spage>3595</spage><epage>3600</epage><pages>3595-3600</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><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.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12027669</pmid><doi>10.1021/jo010757o</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2002-05, Vol.67 (11), p.3595-3600 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71712523 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| 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 |
| title | A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor |
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