Total Synthesis of (±)-Clavilactones A, B, and Proposed D through Iron-Catalyzed Carbonylation-Peroxidation of Olefin
Biologically significant clavilactones A, B, and the previously proposed D have been synthesized through iron‐catalyzed carbonylation–peroxidation of a 1,5‐diene. Three steps from aldehydes, alkenes, and tert‐butylhydroperoxide build up α,β‐epoxy‐γ‐butyrolactone skeleton as a key building block for...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-04, Vol.53 (16), p.4164-4167 |
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| creator | Lv, Leiyang Shen, Baojian Li, Zhiping |
| description | Biologically significant clavilactones A, B, and the previously proposed D have been synthesized through iron‐catalyzed carbonylation–peroxidation of a 1,5‐diene. Three steps from aldehydes, alkenes, and tert‐butylhydroperoxide build up α,β‐epoxy‐γ‐butyrolactone skeleton as a key building block for synthesis of clavilactone family and its derivatives. Based on our results, the structure of the proposed clavilactone D is not correct and requires revision.
A general, concise, and efficient approach for synthesis of clavilactones A, B, and D has been established. Three steps from aldehydes, 1,5‐dienes, and tBuOOH build up α,β‐epoxy‐γ‐butyrolactones (see scheme, left) as the key building blocks for synthesis of clavilactone family and its derivatives. From these results, the previously proposed clavilactone D structure requires revision. |
| doi_str_mv | 10.1002/anie.201400326 |
| format | Article |
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A general, concise, and efficient approach for synthesis of clavilactones A, B, and D has been established. Three steps from aldehydes, 1,5‐dienes, and tBuOOH build up α,β‐epoxy‐γ‐butyrolactones (see scheme, left) as the key building blocks for synthesis of clavilactone family and its derivatives. From these results, the previously proposed clavilactone D structure requires revision.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201400326</identifier><identifier>PMID: 24615883</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkenes - chemistry ; Biological Products - chemical synthesis ; carbonylation-peroxidation ; Catalysis ; clavilactone ; epoxides ; Iron - chemistry ; iron catalysis ; Lactones - chemical synthesis ; Lactones - chemistry ; Molecular Structure ; natural product synthesis ; Stereoisomerism</subject><ispartof>Angewandte Chemie International Edition, 2014-04, Vol.53 (16), p.4164-4167</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4866-b5167ad2ca5981c5ec3da200a8c73ea12020d450592f838223c80b06675619a13</citedby><cites>FETCH-LOGICAL-c4866-b5167ad2ca5981c5ec3da200a8c73ea12020d450592f838223c80b06675619a13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201400326$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201400326$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24615883$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lv, Leiyang</creatorcontrib><creatorcontrib>Shen, Baojian</creatorcontrib><creatorcontrib>Li, Zhiping</creatorcontrib><title>Total Synthesis of (±)-Clavilactones A, B, and Proposed D through Iron-Catalyzed Carbonylation-Peroxidation of Olefin</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Biologically significant clavilactones A, B, and the previously proposed D have been synthesized through iron‐catalyzed carbonylation–peroxidation of a 1,5‐diene. Three steps from aldehydes, alkenes, and tert‐butylhydroperoxide build up α,β‐epoxy‐γ‐butyrolactone skeleton as a key building block for synthesis of clavilactone family and its derivatives. Based on our results, the structure of the proposed clavilactone D is not correct and requires revision.
A general, concise, and efficient approach for synthesis of clavilactones A, B, and D has been established. Three steps from aldehydes, 1,5‐dienes, and tBuOOH build up α,β‐epoxy‐γ‐butyrolactones (see scheme, left) as the key building blocks for synthesis of clavilactone family and its derivatives. From these results, the previously proposed clavilactone D structure requires revision.</description><subject>Alkenes - chemistry</subject><subject>Biological Products - chemical synthesis</subject><subject>carbonylation-peroxidation</subject><subject>Catalysis</subject><subject>clavilactone</subject><subject>epoxides</subject><subject>Iron - chemistry</subject><subject>iron catalysis</subject><subject>Lactones - chemical synthesis</subject><subject>Lactones - chemistry</subject><subject>Molecular Structure</subject><subject>natural product synthesis</subject><subject>Stereoisomerism</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtuEzEUhi1ERS-wZYm8LFIn-DL2eJbpUNpIVRtBEEvrxOMhBmcc7AntdMWmD8Qr8Ch9EiakROxY-fjo-78j_Qi9pGRECWFvoHV2xAjNCeFMPkEHVDCa8aLgT4c55zwrlKD76DClLwOvFJHP0D7LJRVK8QN0NwsdePyhb7uFTS7h0ODjXz9fZ5WH786D6UJr08OP-_EJPj3B0NZ4GsMqJFsPy7e4W8Sw_rzAkxjarILB1d_ZGlcQ56HtPXRu2E9tDLeu_vPZHLj2tnHtc7TXgE_2xeN7hD6-O5tVF9nl9fmkGl9mJldSZnNBZQE1MyBKRY2whtfACAFlCm6BMsJInQsiStYorhjjRpE5kbIQkpZA-RE63npXMXxb29TppUvGeg-tDeuk6eYAK0vJB3S0RU0MKUXb6FV0S4i9pkRv-tabvvWu7yHw6tG9ni9tvcP_FjwA5Ra4cd72_9Hp8dXk7F95ts261NnbXRbiVy0LXgj96epcT8X7SrFZqSn_Db8ynRo</recordid><startdate>20140414</startdate><enddate>20140414</enddate><creator>Lv, Leiyang</creator><creator>Shen, Baojian</creator><creator>Li, Zhiping</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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>20140414</creationdate><title>Total Synthesis of (±)-Clavilactones A, B, and Proposed D through Iron-Catalyzed Carbonylation-Peroxidation of Olefin</title><author>Lv, Leiyang ; Shen, Baojian ; Li, Zhiping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4866-b5167ad2ca5981c5ec3da200a8c73ea12020d450592f838223c80b06675619a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alkenes - chemistry</topic><topic>Biological Products - chemical synthesis</topic><topic>carbonylation-peroxidation</topic><topic>Catalysis</topic><topic>clavilactone</topic><topic>epoxides</topic><topic>Iron - chemistry</topic><topic>iron catalysis</topic><topic>Lactones - chemical synthesis</topic><topic>Lactones - chemistry</topic><topic>Molecular Structure</topic><topic>natural product synthesis</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lv, Leiyang</creatorcontrib><creatorcontrib>Shen, Baojian</creatorcontrib><creatorcontrib>Li, Zhiping</creatorcontrib><collection>Istex</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>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lv, Leiyang</au><au>Shen, Baojian</au><au>Li, Zhiping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of (±)-Clavilactones A, B, and Proposed D through Iron-Catalyzed Carbonylation-Peroxidation of Olefin</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-04-14</date><risdate>2014</risdate><volume>53</volume><issue>16</issue><spage>4164</spage><epage>4167</epage><pages>4164-4167</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Biologically significant clavilactones A, B, and the previously proposed D have been synthesized through iron‐catalyzed carbonylation–peroxidation of a 1,5‐diene. Three steps from aldehydes, alkenes, and tert‐butylhydroperoxide build up α,β‐epoxy‐γ‐butyrolactone skeleton as a key building block for synthesis of clavilactone family and its derivatives. Based on our results, the structure of the proposed clavilactone D is not correct and requires revision.
A general, concise, and efficient approach for synthesis of clavilactones A, B, and D has been established. Three steps from aldehydes, 1,5‐dienes, and tBuOOH build up α,β‐epoxy‐γ‐butyrolactones (see scheme, left) as the key building blocks for synthesis of clavilactone family and its derivatives. From these results, the previously proposed clavilactone D structure requires revision.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24615883</pmid><doi>10.1002/anie.201400326</doi><tpages>4</tpages></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Alkenes - chemistry Biological Products - chemical synthesis carbonylation-peroxidation Catalysis clavilactone epoxides Iron - chemistry iron catalysis Lactones - chemical synthesis Lactones - chemistry Molecular Structure natural product synthesis Stereoisomerism |
| title | Total Synthesis of (±)-Clavilactones A, B, and Proposed D through Iron-Catalyzed Carbonylation-Peroxidation of Olefin |
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