Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583
The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral pool approaches. The succinate 5 and piperazic...
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| Veröffentlicht in: | Journal of organic chemistry 2004-03, Vol.69 (5), p.1734-1737 |
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| container_issue | 5 |
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| container_title | Journal of organic chemistry |
| container_volume | 69 |
| creator | Coats, Reed A Lee, Sheng-Lian Davis, Kari A Patel, Kanu M Rhoads, Elaine K Howard, Michael H |
| description | The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral pool approaches. The succinate 5 and piperazic acid 9 moieties were obtained by Evans oxazolidinone imide enolate alkylation and hydrazination/cyclization, respectively, and the aminohexanone side chain 13 was prepared via Grignard substitution of the Weinreb amide derived from l-valine. Spectroscopic data for the resulting synthetic material, compared with the data reported for the natural product, established that the previously unassigned valine ketone stereocenter (C-4) has the S-configuration. |
| doi_str_mv | 10.1021/jo035667t |
| format | Article |
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The three chiral centers were set by a combination of chiral auxiliary and chiral pool approaches. The succinate 5 and piperazic acid 9 moieties were obtained by Evans oxazolidinone imide enolate alkylation and hydrazination/cyclization, respectively, and the aminohexanone side chain 13 was prepared via Grignard substitution of the Weinreb amide derived from l-valine. Spectroscopic data for the resulting synthetic material, compared with the data reported for the natural product, established that the previously unassigned valine ketone stereocenter (C-4) has the S-configuration.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo035667t</identifier><identifier>PMID: 14987037</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amidohydrolases - antagonists & inhibitors ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Biological and medical sciences ; Chemistry ; Cyclization ; Dipeptides - chemical synthesis ; Dipeptides - chemistry ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Hexanones - chemistry ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular Structure ; Organic chemistry ; Peptides ; Pharmacology. Drug treatments ; Preparations and properties ; Pyridazines - chemical synthesis ; Pyridazines - chemistry ; Stereoisomerism ; Succinates - chemistry</subject><ispartof>Journal of organic chemistry, 2004-03, Vol.69 (5), p.1734-1737</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a409t-6fb9e77eaf0b9cc9c4c2922a53e6d017f5cff07a86bb61b5877e7da9d9c816643</citedby><cites>FETCH-LOGICAL-a409t-6fb9e77eaf0b9cc9c4c2922a53e6d017f5cff07a86bb61b5877e7da9d9c816643</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo035667t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo035667t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15518237$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16639608$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14987037$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Coats, Reed A</creatorcontrib><creatorcontrib>Lee, Sheng-Lian</creatorcontrib><creatorcontrib>Davis, Kari A</creatorcontrib><creatorcontrib>Patel, Kanu M</creatorcontrib><creatorcontrib>Rhoads, Elaine K</creatorcontrib><creatorcontrib>Howard, Michael H</creatorcontrib><title>Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral pool approaches. The succinate 5 and piperazic acid 9 moieties were obtained by Evans oxazolidinone imide enolate alkylation and hydrazination/cyclization, respectively, and the aminohexanone side chain 13 was prepared via Grignard substitution of the Weinreb amide derived from l-valine. Spectroscopic data for the resulting synthetic material, compared with the data reported for the natural product, established that the previously unassigned valine ketone stereocenter (C-4) has the S-configuration.</description><subject>Amidohydrolases - antagonists & inhibitors</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Dipeptides - chemical synthesis</subject><subject>Dipeptides - chemistry</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Hexanones - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Peptides</subject><subject>Pharmacology. Drug treatments</subject><subject>Preparations and properties</subject><subject>Pyridazines - chemical synthesis</subject><subject>Pyridazines - chemistry</subject><subject>Stereoisomerism</subject><subject>Succinates - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0MuKFDEUBuAgitOOLnwByUbBRWkuldvSaS8z0upAjbgMqdQJlbEubVIN9tubsZvpjWA2CeTLT86P0HNK3lDC6NvbmXAhpVoeoBUVjFTSkPohWhHCWMWZ5GfoSc63pCwhxGN0RmujFeFqhaBZIMHsexijdwN-DyFOcYnzhN3U4XUf05y34GOIHjf7aekhx4zngMsJX8N2iR3cvZrTuB9cBnw19bGNy5xw43vMNROaP0WPghsyPDvu5-j7xw8368tq8-3T1frdpnI1MUslQ2tAKXCBtMZ742vPDGNOcJAdoSoIHwJRTsu2lbQVuljVOdMZr6mUNT9Hrw652zT_2kFe7Bizh2FwE8y7bBWVutaaFvj6AH0ZLycIdpvi6NLeUmLvOrX3nRb74hi6a0foTvJYYgEvj8Dl0mFIbvIxn5yU3Eii_-uEoJr9zasOLuYFft_fu_TTSsWVsDfXjd1cfqU_vlw09vMp1_lc_r1LU-n4H4P8ATjlpus</recordid><startdate>20040305</startdate><enddate>20040305</enddate><creator>Coats, Reed A</creator><creator>Lee, Sheng-Lian</creator><creator>Davis, Kari A</creator><creator>Patel, Kanu M</creator><creator>Rhoads, Elaine K</creator><creator>Howard, Michael H</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040305</creationdate><title>Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583</title><author>Coats, Reed A ; Lee, Sheng-Lian ; Davis, Kari A ; Patel, Kanu M ; Rhoads, Elaine K ; Howard, Michael H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a409t-6fb9e77eaf0b9cc9c4c2922a53e6d017f5cff07a86bb61b5877e7da9d9c816643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Amidohydrolases - antagonists & inhibitors</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Dipeptides - chemical synthesis</topic><topic>Dipeptides - chemistry</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Hexanones - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Peptides</topic><topic>Pharmacology. Drug treatments</topic><topic>Preparations and properties</topic><topic>Pyridazines - chemical synthesis</topic><topic>Pyridazines - chemistry</topic><topic>Stereoisomerism</topic><topic>Succinates - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Coats, Reed A</creatorcontrib><creatorcontrib>Lee, Sheng-Lian</creatorcontrib><creatorcontrib>Davis, Kari A</creatorcontrib><creatorcontrib>Patel, Kanu M</creatorcontrib><creatorcontrib>Rhoads, Elaine K</creatorcontrib><creatorcontrib>Howard, Michael H</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Coats, Reed A</au><au>Lee, Sheng-Lian</au><au>Davis, Kari A</au><au>Patel, Kanu M</au><au>Rhoads, Elaine K</au><au>Howard, Michael H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-03-05</date><risdate>2004</risdate><volume>69</volume><issue>5</issue><spage>1734</spage><epage>1737</epage><pages>1734-1737</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral pool approaches. The succinate 5 and piperazic acid 9 moieties were obtained by Evans oxazolidinone imide enolate alkylation and hydrazination/cyclization, respectively, and the aminohexanone side chain 13 was prepared via Grignard substitution of the Weinreb amide derived from l-valine. Spectroscopic data for the resulting synthetic material, compared with the data reported for the natural product, established that the previously unassigned valine ketone stereocenter (C-4) has the S-configuration.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14987037</pmid><doi>10.1021/jo035667t</doi><tpages>4</tpages></addata></record> |
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| subjects | Amidohydrolases - antagonists & inhibitors Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Chemistry Cyclization Dipeptides - chemical synthesis Dipeptides - chemistry Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Hexanones - chemistry Magnetic Resonance Spectroscopy Medical sciences Molecular Structure Organic chemistry Peptides Pharmacology. Drug treatments Preparations and properties Pyridazines - chemical synthesis Pyridazines - chemistry Stereoisomerism Succinates - chemistry |
| title | Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583 |
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