Expeditious Synthesis of Ieodoglucomides A and B from the Marine‐Derived Bacterium Bacillus licheniformis
We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The short and efficient synthesis invo...
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| Veröffentlicht in: | European journal of organic chemistry 2018-06, Vol.2018 (24), p.3230-3235 |
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| container_title | European journal of organic chemistry |
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| creator | Podilapu, Ananda Rao Emmadi, Madhu Kulkarni, Suvarn S. |
| description | We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The short and efficient synthesis involves 11 steps, with 38–40 % overall yield.
The total synthesis of the marine‐derived bacterial glycopeptides ieodoglucomides A and B is reported. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The synthesis involves 11 steps, with 38–40 % overall yield. |
| doi_str_mv | 10.1002/ejoc.201800209 |
| format | Article |
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The total synthesis of the marine‐derived bacterial glycopeptides ieodoglucomides A and B is reported. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The synthesis involves 11 steps, with 38–40 % overall yield.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201800209</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Acylation ; Bacteria ; Carbohydrates ; Chemical synthesis ; Glycosyl iodides ; Glycosylation ; Marine chemistry ; Metathesis ; Natural products ; Structure elucidation ; Total synthesis</subject><ispartof>European journal of organic chemistry, 2018-06, Vol.2018 (24), p.3230-3235</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3179-976eb4de595aef5ef0d7d31b5a295b8ccda69d0d55ec17456888377813113f3</citedby><cites>FETCH-LOGICAL-c3179-976eb4de595aef5ef0d7d31b5a295b8ccda69d0d55ec17456888377813113f3</cites><orcidid>0000-0003-2884-876X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201800209$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201800209$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Podilapu, Ananda Rao</creatorcontrib><creatorcontrib>Emmadi, Madhu</creatorcontrib><creatorcontrib>Kulkarni, Suvarn S.</creatorcontrib><title>Expeditious Synthesis of Ieodoglucomides A and B from the Marine‐Derived Bacterium Bacillus licheniformis</title><title>European journal of organic chemistry</title><description>We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The short and efficient synthesis involves 11 steps, with 38–40 % overall yield.
The total synthesis of the marine‐derived bacterial glycopeptides ieodoglucomides A and B is reported. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The synthesis involves 11 steps, with 38–40 % overall yield.</description><subject>Acylation</subject><subject>Bacteria</subject><subject>Carbohydrates</subject><subject>Chemical synthesis</subject><subject>Glycosyl iodides</subject><subject>Glycosylation</subject><subject>Marine chemistry</subject><subject>Metathesis</subject><subject>Natural products</subject><subject>Structure elucidation</subject><subject>Total synthesis</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OAzEQhE8IJEKgpbZEfWF9vj-XIQQICqIIBZ11sdfE4e4c7ByQjkfgGXkSHAVBSbWz2m9mpYmiUwoDCpCc49LKQQK0DAvwvahHgfMYcg77QacsjSlnj4fRkfdLAOB5TnvR8_h9hcqsje08mW3a9QK98cRqMkGr7FPdSdsYhZ4MSdUqckG0sw0JGLmrnGnx6-PzEp15xXCr5DrIrtkqU9chsTZyga3R1jXGH0cHuqo9nvzMfjS7Gj-MbuLp_fVkNJzGktGCx7zIcZ4qzHhWoc5QgyoUo_OsSng2L6VUVc4VqCxDSYs0y8uyZEVRUkYp06wfne1SV86-dOjXYmk714aHIoGcJpxTyAM12FHSWe8darFypqncRlAQ2zrFtk7xW2cw8J3hzdS4-YcW49v70Z_3G6Pme1w</recordid><startdate>20180629</startdate><enddate>20180629</enddate><creator>Podilapu, Ananda Rao</creator><creator>Emmadi, Madhu</creator><creator>Kulkarni, Suvarn S.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2884-876X</orcidid></search><sort><creationdate>20180629</creationdate><title>Expeditious Synthesis of Ieodoglucomides A and B from the Marine‐Derived Bacterium Bacillus licheniformis</title><author>Podilapu, Ananda Rao ; Emmadi, Madhu ; Kulkarni, Suvarn S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3179-976eb4de595aef5ef0d7d31b5a295b8ccda69d0d55ec17456888377813113f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acylation</topic><topic>Bacteria</topic><topic>Carbohydrates</topic><topic>Chemical synthesis</topic><topic>Glycosyl iodides</topic><topic>Glycosylation</topic><topic>Marine chemistry</topic><topic>Metathesis</topic><topic>Natural products</topic><topic>Structure elucidation</topic><topic>Total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Podilapu, Ananda Rao</creatorcontrib><creatorcontrib>Emmadi, Madhu</creatorcontrib><creatorcontrib>Kulkarni, Suvarn S.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Podilapu, Ananda Rao</au><au>Emmadi, Madhu</au><au>Kulkarni, Suvarn S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Expeditious Synthesis of Ieodoglucomides A and B from the Marine‐Derived Bacterium Bacillus licheniformis</atitle><jtitle>European journal of organic chemistry</jtitle><date>2018-06-29</date><risdate>2018</risdate><volume>2018</volume><issue>24</issue><spage>3230</spage><epage>3235</epage><pages>3230-3235</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The short and efficient synthesis involves 11 steps, with 38–40 % overall yield.
The total synthesis of the marine‐derived bacterial glycopeptides ieodoglucomides A and B is reported. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The synthesis involves 11 steps, with 38–40 % overall yield.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201800209</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-2884-876X</orcidid></addata></record> |
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| subjects | Acylation Bacteria Carbohydrates Chemical synthesis Glycosyl iodides Glycosylation Marine chemistry Metathesis Natural products Structure elucidation Total synthesis |
| title | Expeditious Synthesis of Ieodoglucomides A and B from the Marine‐Derived Bacterium Bacillus licheniformis |
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