Total Syntheses of Dendrodolides A, B, and E
Convergent total syntheses of dendrodolides A, B, and E comprising 12‐membered macrolactones are described. The syntheses of dendrodolides A and B were accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from commercially available homoallyl alcohol 19 and enanti...
Gespeichert in:
| Veröffentlicht in: | Asian journal of organic chemistry 2014-11, Vol.3 (11), p.1210-1216 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1216 |
|---|---|
| container_issue | 11 |
| container_start_page | 1210 |
| container_title | Asian journal of organic chemistry |
| container_volume | 3 |
| creator | Mohapatra, Debendra K. Pulluri, Karthik Bhimireddy, Eswar Reddy, D. Prabhakar Yadav, Jhillu S. |
| description | Convergent total syntheses of dendrodolides A, B, and E comprising 12‐membered macrolactones are described. The syntheses of dendrodolides A and B were accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from commercially available homoallyl alcohol 19 and enantiomerically pure epoxide 20. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Key steps were Maruoka asymmetric allylation, Corey‐Chaykovsky reaction, Yamaguchi esterification, and ring‐closing metathesis.
Chemist's XI: Efficient stereoselective total syntheses of dendrodolides A and B have been accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from a commercially available homoallyl alcohol. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Bn=benzyl: PMB=para‐methoxybenzyl; RCM=ring‐closing metathesis. |
| doi_str_mv | 10.1002/ajoc.201402126 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1622023409</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3489723581</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3556-a3bf9df2e2959afc02351d676a70977c7f15be138a34790ac80f5000b7c72fa13</originalsourceid><addsrcrecordid>eNqFkE1PwzAMhiMEEtPYlXMlrutwkqVZjlv3xTSxA0Mco6xNREdpRtJp9N-TqWjihi-27PexrRehewwDDEAe1d5mAwJ4CAST5Ap1CBY0ZiPMri818FvU834PITgXmIgO6m9trcropanqd-21j6yJprrKnc1tWeShMe5Hk36kqjya3aEbo0qve7-5i17ns226jNebxVM6XscZZSyJFd0ZkRuiiWBCmQwIZThPeKI4CM4zbjDbaUxHig65AJWNwLDw0y6MiFGYdtFDu_fg7NdR-1ru7dFV4aTECSFh3xBEUA1aVeas904beXDFp3KNxCDPpsizKfJiSgBEC5yKUjf_qOV4tUn_snHLFr7W3xdWuQ-ZcMqZfHteyOV0BWw-SSXQHzn6cOk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1622023409</pqid></control><display><type>article</type><title>Total Syntheses of Dendrodolides A, B, and E</title><source>Wiley Online Library All Journals</source><creator>Mohapatra, Debendra K. ; Pulluri, Karthik ; Bhimireddy, Eswar ; Reddy, D. Prabhakar ; Yadav, Jhillu S.</creator><creatorcontrib>Mohapatra, Debendra K. ; Pulluri, Karthik ; Bhimireddy, Eswar ; Reddy, D. Prabhakar ; Yadav, Jhillu S.</creatorcontrib><description>Convergent total syntheses of dendrodolides A, B, and E comprising 12‐membered macrolactones are described. The syntheses of dendrodolides A and B were accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from commercially available homoallyl alcohol 19 and enantiomerically pure epoxide 20. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Key steps were Maruoka asymmetric allylation, Corey‐Chaykovsky reaction, Yamaguchi esterification, and ring‐closing metathesis.
Chemist's XI: Efficient stereoselective total syntheses of dendrodolides A and B have been accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from a commercially available homoallyl alcohol. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Bn=benzyl: PMB=para‐methoxybenzyl; RCM=ring‐closing metathesis.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.201402126</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>dendrodolides ; Maruoka asymmetric allylation ; Organic chemistry ; ring-closing metathesis ; total synthesis ; Yamaguchi esterification</subject><ispartof>Asian journal of organic chemistry, 2014-11, Vol.3 (11), p.1210-1216</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-c3556-a3bf9df2e2959afc02351d676a70977c7f15be138a34790ac80f5000b7c72fa13</citedby><cites>FETCH-LOGICAL-c3556-a3bf9df2e2959afc02351d676a70977c7f15be138a34790ac80f5000b7c72fa13</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%2Fajoc.201402126$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.201402126$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Mohapatra, Debendra K.</creatorcontrib><creatorcontrib>Pulluri, Karthik</creatorcontrib><creatorcontrib>Bhimireddy, Eswar</creatorcontrib><creatorcontrib>Reddy, D. Prabhakar</creatorcontrib><creatorcontrib>Yadav, Jhillu S.</creatorcontrib><title>Total Syntheses of Dendrodolides A, B, and E</title><title>Asian journal of organic chemistry</title><addtitle>Asian Journal of Organic Chemistry</addtitle><description>Convergent total syntheses of dendrodolides A, B, and E comprising 12‐membered macrolactones are described. The syntheses of dendrodolides A and B were accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from commercially available homoallyl alcohol 19 and enantiomerically pure epoxide 20. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Key steps were Maruoka asymmetric allylation, Corey‐Chaykovsky reaction, Yamaguchi esterification, and ring‐closing metathesis.
Chemist's XI: Efficient stereoselective total syntheses of dendrodolides A and B have been accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from a commercially available homoallyl alcohol. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Bn=benzyl: PMB=para‐methoxybenzyl; RCM=ring‐closing metathesis.</description><subject>dendrodolides</subject><subject>Maruoka asymmetric allylation</subject><subject>Organic chemistry</subject><subject>ring-closing metathesis</subject><subject>total synthesis</subject><subject>Yamaguchi esterification</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkE1PwzAMhiMEEtPYlXMlrutwkqVZjlv3xTSxA0Mco6xNREdpRtJp9N-TqWjihi-27PexrRehewwDDEAe1d5mAwJ4CAST5Ap1CBY0ZiPMri818FvU834PITgXmIgO6m9trcropanqd-21j6yJprrKnc1tWeShMe5Hk36kqjya3aEbo0qve7-5i17ns226jNebxVM6XscZZSyJFd0ZkRuiiWBCmQwIZThPeKI4CM4zbjDbaUxHig65AJWNwLDw0y6MiFGYdtFDu_fg7NdR-1ru7dFV4aTECSFh3xBEUA1aVeas904beXDFp3KNxCDPpsizKfJiSgBEC5yKUjf_qOV4tUn_snHLFr7W3xdWuQ-ZcMqZfHteyOV0BWw-SSXQHzn6cOk</recordid><startdate>201411</startdate><enddate>201411</enddate><creator>Mohapatra, Debendra K.</creator><creator>Pulluri, Karthik</creator><creator>Bhimireddy, Eswar</creator><creator>Reddy, D. Prabhakar</creator><creator>Yadav, Jhillu S.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201411</creationdate><title>Total Syntheses of Dendrodolides A, B, and E</title><author>Mohapatra, Debendra K. ; Pulluri, Karthik ; Bhimireddy, Eswar ; Reddy, D. Prabhakar ; Yadav, Jhillu S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3556-a3bf9df2e2959afc02351d676a70977c7f15be138a34790ac80f5000b7c72fa13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>dendrodolides</topic><topic>Maruoka asymmetric allylation</topic><topic>Organic chemistry</topic><topic>ring-closing metathesis</topic><topic>total synthesis</topic><topic>Yamaguchi esterification</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mohapatra, Debendra K.</creatorcontrib><creatorcontrib>Pulluri, Karthik</creatorcontrib><creatorcontrib>Bhimireddy, Eswar</creatorcontrib><creatorcontrib>Reddy, D. Prabhakar</creatorcontrib><creatorcontrib>Yadav, Jhillu S.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mohapatra, Debendra K.</au><au>Pulluri, Karthik</au><au>Bhimireddy, Eswar</au><au>Reddy, D. Prabhakar</au><au>Yadav, Jhillu S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Syntheses of Dendrodolides A, B, and E</atitle><jtitle>Asian journal of organic chemistry</jtitle><addtitle>Asian Journal of Organic Chemistry</addtitle><date>2014-11</date><risdate>2014</risdate><volume>3</volume><issue>11</issue><spage>1210</spage><epage>1216</epage><pages>1210-1216</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>Convergent total syntheses of dendrodolides A, B, and E comprising 12‐membered macrolactones are described. The syntheses of dendrodolides A and B were accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from commercially available homoallyl alcohol 19 and enantiomerically pure epoxide 20. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Key steps were Maruoka asymmetric allylation, Corey‐Chaykovsky reaction, Yamaguchi esterification, and ring‐closing metathesis.
Chemist's XI: Efficient stereoselective total syntheses of dendrodolides A and B have been accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from a commercially available homoallyl alcohol. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Bn=benzyl: PMB=para‐methoxybenzyl; RCM=ring‐closing metathesis.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ajoc.201402126</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2193-5807 |
| ispartof | Asian journal of organic chemistry, 2014-11, Vol.3 (11), p.1210-1216 |
| issn | 2193-5807 2193-5815 |
| language | eng |
| recordid | cdi_proquest_journals_1622023409 |
| source | Wiley Online Library All Journals |
| subjects | dendrodolides Maruoka asymmetric allylation Organic chemistry ring-closing metathesis total synthesis Yamaguchi esterification |
| title | Total Syntheses of Dendrodolides A, B, and E |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T07%3A29%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Total%20Syntheses%20of%20Dendrodolides%20A,%20B,%20and%20E&rft.jtitle=Asian%20journal%20of%20organic%20chemistry&rft.au=Mohapatra,%20Debendra%20K.&rft.date=2014-11&rft.volume=3&rft.issue=11&rft.spage=1210&rft.epage=1216&rft.pages=1210-1216&rft.issn=2193-5807&rft.eissn=2193-5815&rft_id=info:doi/10.1002/ajoc.201402126&rft_dat=%3Cproquest_cross%3E3489723581%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1622023409&rft_id=info:pmid/&rfr_iscdi=true |