Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin
An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselect...
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| Veröffentlicht in: | Journal of organic chemistry 2012-04, Vol.77 (7), p.3297-3310 |
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| container_end_page | 3310 |
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| container_issue | 7 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Zhong, Yong-Li Gauthier, Donald R Shi, Yao-Jun McLaughlin, Mark Chung, John Y. L Dagneau, Philippe Marcune, Benjamin Krska, Shane W Ball, Richard G Reamer, Robert A Yasuda, Nobuyoshi |
| description | An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselective, improved palladium(II)-mediated Corey-Yu allylic oxidation at the highly congested C-12 position of the enfumafungin core. Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively. |
| doi_str_mv | 10.1021/jo300046v |
| format | Article |
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Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo300046v</identifier><identifier>PMID: 22423625</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alcohols - chemistry ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal agents ; Antifungal Agents - chemical synthesis ; Antifungal Agents - pharmacology ; Biological and medical sciences ; Catalysis ; Chemistry ; Chrysenes - chemical synthesis ; Chrysenes - chemistry ; Echinocandins - chemistry ; Exact sciences and technology ; Glucosyltransferases - antagonists & inhibitors ; Glycosides - chemistry ; Medical sciences ; Molecular Structure ; Organic chemistry ; Palladium - chemistry ; Pharmacology. Drug treatments ; Preparations and properties ; Stereoisomerism ; Terpenoids ; Triterpenes - chemistry</subject><ispartof>Journal of organic chemistry, 2012-04, Vol.77 (7), p.3297-3310</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-126042fb277445ad5505ae6644ec0f088696fdefb7f8a0070d07248a800dfd163</citedby><cites>FETCH-LOGICAL-a410t-126042fb277445ad5505ae6644ec0f088696fdefb7f8a0070d07248a800dfd163</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/jo300046v$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo300046v$$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=25778578$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22423625$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhong, Yong-Li</creatorcontrib><creatorcontrib>Gauthier, Donald R</creatorcontrib><creatorcontrib>Shi, Yao-Jun</creatorcontrib><creatorcontrib>McLaughlin, Mark</creatorcontrib><creatorcontrib>Chung, John Y. 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Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.</description><subject>Alcohols - chemistry</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chrysenes - chemical synthesis</subject><subject>Chrysenes - chemistry</subject><subject>Echinocandins - chemistry</subject><subject>Exact sciences and technology</subject><subject>Glucosyltransferases - antagonists & inhibitors</subject><subject>Glycosides - chemistry</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Palladium - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Terpenoids</subject><subject>Triterpenes - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E9LwzAYx_EgipvTg29AehHxUH2S5l-PY845GHhQzyVtE5fRpjNphb17Oze3i6cc8uH3wBehawwPGAh-XDUJAFD-fYKGmBGIeQr0FA0BCIkTwpMBughh1RtgjJ2jASGUJJywIXp627h2qYMNUWOisWut6dynqqJZ1RXKRb_fKuho7pY2t23jQ2R8U0dTZ7pabbF1l-jMqCroq_07Qh_P0_fJS7x4nc0n40WsKIY2xoQDJSYnQlDKVMkYMKU5p1QXYEBKnnJTapMLIxWAgBIEoVJJgNKUmCcjdLfbXfvmq9OhzWobCl1VyummC1maEklSkdBe3u9k4ZsQvDbZ2tta-U2GIds2yw7NenuzX-3yWpcH-RepB7d7oEKhKuOVK2w4OiaEZEIenSpCv99518f45-APngR-xg</recordid><startdate>20120406</startdate><enddate>20120406</enddate><creator>Zhong, Yong-Li</creator><creator>Gauthier, Donald R</creator><creator>Shi, Yao-Jun</creator><creator>McLaughlin, Mark</creator><creator>Chung, John Y. L</creator><creator>Dagneau, Philippe</creator><creator>Marcune, Benjamin</creator><creator>Krska, Shane W</creator><creator>Ball, Richard G</creator><creator>Reamer, Robert A</creator><creator>Yasuda, Nobuyoshi</creator><general>American Chemical Society</general><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>20120406</creationdate><title>Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin</title><author>Zhong, Yong-Li ; Gauthier, Donald R ; Shi, Yao-Jun ; McLaughlin, Mark ; Chung, John Y. L ; Dagneau, Philippe ; Marcune, Benjamin ; Krska, Shane W ; Ball, Richard G ; Reamer, Robert A ; Yasuda, Nobuyoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-126042fb277445ad5505ae6644ec0f088696fdefb7f8a0070d07248a800dfd163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alcohols - chemistry</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chrysenes - chemical synthesis</topic><topic>Chrysenes - chemistry</topic><topic>Echinocandins - chemistry</topic><topic>Exact sciences and technology</topic><topic>Glucosyltransferases - antagonists & inhibitors</topic><topic>Glycosides - chemistry</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Palladium - chemistry</topic><topic>Pharmacology. 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L</au><au>Dagneau, Philippe</au><au>Marcune, Benjamin</au><au>Krska, Shane W</au><au>Ball, Richard G</au><au>Reamer, Robert A</au><au>Yasuda, Nobuyoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-04-06</date><risdate>2012</risdate><volume>77</volume><issue>7</issue><spage>3297</spage><epage>3310</epage><pages>3297-3310</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselective, improved palladium(II)-mediated Corey-Yu allylic oxidation at the highly congested C-12 position of the enfumafungin core. Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22423625</pmid><doi>10.1021/jo300046v</doi><tpages>14</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alcohols - chemistry Alicyclic compounds, terpenoids, prostaglandins, steroids Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - pharmacology Biological and medical sciences Catalysis Chemistry Chrysenes - chemical synthesis Chrysenes - chemistry Echinocandins - chemistry Exact sciences and technology Glucosyltransferases - antagonists & inhibitors Glycosides - chemistry Medical sciences Molecular Structure Organic chemistry Palladium - chemistry Pharmacology. Drug treatments Preparations and properties Stereoisomerism Terpenoids Triterpenes - chemistry |
| title | Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin |
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