A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms
A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement. Get shorty:...
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| Veröffentlicht in: | Chemistry : a European journal 2016-08, Vol.22 (33), p.11597-11600 |
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| container_issue | 33 |
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| container_title | Chemistry : a European journal |
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| creator | Ferrara, Steven J. Burton, Jonathan W. |
| description | A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement.
Get shorty: A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement. |
| doi_str_mv | 10.1002/chem.201602669 |
| format | Article |
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Get shorty: A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201602669</identifier><identifier>PMID: 27389970</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>aphanamol ; Biological Products ; Catalysis ; Catalysts ; Chemistry ; Claisen rearrangement ; Communication ; Communications ; conjugate addition ; Conjugates ; Cyclization ; Enantiomers ; Natural products ; Oxidation-Reduction ; radical cyclization ; Radicals ; Sesquiterpenes - chemical synthesis ; Sesquiterpenes - chemistry ; Stereoisomerism ; Synthesis ; total synthesis</subject><ispartof>Chemistry : a European journal, 2016-08, Vol.22 (33), p.11597-11600</ispartof><rights>2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6049-7954502dee0e3fd20a82e648103ff72d0bd602d9ab43ba9109b2355c96e7acd63</citedby><cites>FETCH-LOGICAL-c6049-7954502dee0e3fd20a82e648103ff72d0bd602d9ab43ba9109b2355c96e7acd63</cites><orcidid>0000-0002-5181-5301</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%2Fchem.201602669$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201602669$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,315,781,785,886,1418,27925,27926,45575,45576</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27389970$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ferrara, Steven J.</creatorcontrib><creatorcontrib>Burton, Jonathan W.</creatorcontrib><title>A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement.
Get shorty: A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement.</description><subject>aphanamol</subject><subject>Biological Products</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Claisen rearrangement</subject><subject>Communication</subject><subject>Communications</subject><subject>conjugate addition</subject><subject>Conjugates</subject><subject>Cyclization</subject><subject>Enantiomers</subject><subject>Natural products</subject><subject>Oxidation-Reduction</subject><subject>radical cyclization</subject><subject>Radicals</subject><subject>Sesquiterpenes - chemical synthesis</subject><subject>Sesquiterpenes - chemistry</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><subject>total synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><sourceid>EIF</sourceid><recordid>eNqNkc1v1DAQxS0EokvhyhFZ4sIly9iOvy5Iy7LpViogsaAeLW_ikJTEXuyEdv97Um1ZFQ7AaQ7ze2_05iH0nMCcANDXZeP6OQUigAqhH6AZ4ZRkTAr-EM1A5zITnOkT9CSlKwDQgrHH6IRKprSWMEPFAm-aEAe82fuhcalNONR4sWust33o8DluPX4bhgZ_sqXr2xJbX-GVt35ow26MDhch9ukpelTbLrlnd_MUfSlWn5fr7OLj2flycZGVAnKdSc1zDrRyDhyrKwpWUSdyRYDVtaQVbKspSKXtNmdbqwnoLWWcl1o4actKsFP05uC7G7e9q0rnh2g7s4ttb-PeBNua3ze-bczX8MPwKToVdDJ4dWcQw_fRpcH0bSpd11nvwpgMUdM9AUqq_0BBMSUpyyf05R_oVRijnz5hiAbJciqA_5VSIJXQXJCJmh-oMoaUoquP6QiY287Nbefm2PkkeHH_J0f8V8kToA_Addu5_T_szHK9en_fPDto2zS4m6PWxm9GSCa5ufxwZuTm3WWRF9ys2U_T48UX</recordid><startdate>20160808</startdate><enddate>20160808</enddate><creator>Ferrara, Steven J.</creator><creator>Burton, Jonathan W.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>BSCLL</scope><scope>24P</scope><scope>WIN</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-5181-5301</orcidid></search><sort><creationdate>20160808</creationdate><title>A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms</title><author>Ferrara, Steven J. ; Burton, Jonathan W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6049-7954502dee0e3fd20a82e648103ff72d0bd602d9ab43ba9109b2355c96e7acd63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>aphanamol</topic><topic>Biological Products</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Claisen rearrangement</topic><topic>Communication</topic><topic>Communications</topic><topic>conjugate addition</topic><topic>Conjugates</topic><topic>Cyclization</topic><topic>Enantiomers</topic><topic>Natural products</topic><topic>Oxidation-Reduction</topic><topic>radical cyclization</topic><topic>Radicals</topic><topic>Sesquiterpenes - chemical synthesis</topic><topic>Sesquiterpenes - chemistry</topic><topic>Stereoisomerism</topic><topic>Synthesis</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ferrara, Steven J.</creatorcontrib><creatorcontrib>Burton, Jonathan W.</creatorcontrib><collection>Istex</collection><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Online Library Free Content</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ferrara, Steven J.</au><au>Burton, Jonathan W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. 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Get shorty: A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27389970</pmid><doi>10.1002/chem.201602669</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-5181-5301</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemistry : a European journal, 2016-08, Vol.22 (33), p.11597-11600 |
| issn | 0947-6539 1521-3765 |
| language | eng |
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| source | MEDLINE; Access via Wiley Online Library |
| subjects | aphanamol Biological Products Catalysis Catalysts Chemistry Claisen rearrangement Communication Communications conjugate addition Conjugates Cyclization Enantiomers Natural products Oxidation-Reduction radical cyclization Radicals Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Stereoisomerism Synthesis total synthesis |
| title | A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms |
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