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A practical, tandem and protecting-group-free synthesis of (+)-rosmarinic acid and its analogues
[Display omitted] A short, tandem and protecting-group-free total synthesis of (+)-rosmarinic acid and related ester derivatives from (+)-danshensu (or corresponding aryl lactic acid) and related hydroxybenzaldehydes in 54 %∼87 % overall yield is described. The key step is the Meldrum’s acid mediate...
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Published in: | Tetrahedron letters 2024-01, Vol.135, p.154879, Article 154879 |
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container_start_page | 154879 |
container_title | Tetrahedron letters |
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creator | Sun, Ying Fan, Peinan Zhao, Xiaolong Liu, Dan Ru, Yilin Bai, Yujun Bai, Yajun Zheng, Xiaohui |
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A short, tandem and protecting-group-free total synthesis of (+)-rosmarinic acid and related ester derivatives from (+)-danshensu (or corresponding aryl lactic acid) and related hydroxybenzaldehydes in 54 %∼87 % overall yield is described. The key step is the Meldrum’s acid mediate tandem classical Knoevenagel condensation. |
doi_str_mv | 10.1016/j.tetlet.2023.154879 |
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A short, tandem and protecting-group-free total synthesis of (+)-rosmarinic acid and related ester derivatives from (+)-danshensu (or corresponding aryl lactic acid) and related hydroxybenzaldehydes in 54 %∼87 % overall yield is described. The key step is the Meldrum’s acid mediate tandem classical Knoevenagel condensation.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2023.154879</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>(+)-rosmarinic acid ; Knoevenagel condensation ; Protecting-group-free ; Synthesis ; Tandem reaction</subject><ispartof>Tetrahedron letters, 2024-01, Vol.135, p.154879, Article 154879</ispartof><rights>2023 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c306t-aa44b7ef71748e8c52ee2429d607d5423644e4aca78e37730ff22a6163a029313</citedby><cites>FETCH-LOGICAL-c306t-aa44b7ef71748e8c52ee2429d607d5423644e4aca78e37730ff22a6163a029313</cites><orcidid>0000-0002-3489-1038</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Sun, Ying</creatorcontrib><creatorcontrib>Fan, Peinan</creatorcontrib><creatorcontrib>Zhao, Xiaolong</creatorcontrib><creatorcontrib>Liu, Dan</creatorcontrib><creatorcontrib>Ru, Yilin</creatorcontrib><creatorcontrib>Bai, Yujun</creatorcontrib><creatorcontrib>Bai, Yajun</creatorcontrib><creatorcontrib>Zheng, Xiaohui</creatorcontrib><title>A practical, tandem and protecting-group-free synthesis of (+)-rosmarinic acid and its analogues</title><title>Tetrahedron letters</title><description>[Display omitted]
A short, tandem and protecting-group-free total synthesis of (+)-rosmarinic acid and related ester derivatives from (+)-danshensu (or corresponding aryl lactic acid) and related hydroxybenzaldehydes in 54 %∼87 % overall yield is described. The key step is the Meldrum’s acid mediate tandem classical Knoevenagel condensation.</description><subject>(+)-rosmarinic acid</subject><subject>Knoevenagel condensation</subject><subject>Protecting-group-free</subject><subject>Synthesis</subject><subject>Tandem reaction</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLxDAUhYMoOI7-AxddKpqaV5t0IwyDLxhwo-sY05uaodMOSUaYf2_GuvYu7oUD53Duh9AlJSUltL5blwlSD6lkhPGSVkLJ5gjNqJIc80rRYzQjRBAsCG9O0VmMa5KnVmSGPhbFNhibvDX9bZHM0MKmyDurY4KsDx3uwrjbYhcAirgf0hdEH4vRFVc31ziMcWOCH7wtjPXtr9WnmK_px24H8RydONNHuPi7c_T--PC2fMar16eX5WKFLSd1wsYI8SnBSSqFAmUrBsAEa9qayLYSjNdCgDDWSAVcSk6cY8zUtOaGsIZTPkdiyrW5Ugzg9Db4XG2vKdEHSnqtJ0r6QElPlLLtfrJB7vbtIehoPQwWWh_y-7od_f8BPxpSclo</recordid><startdate>20240131</startdate><enddate>20240131</enddate><creator>Sun, Ying</creator><creator>Fan, Peinan</creator><creator>Zhao, Xiaolong</creator><creator>Liu, Dan</creator><creator>Ru, Yilin</creator><creator>Bai, Yujun</creator><creator>Bai, Yajun</creator><creator>Zheng, Xiaohui</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-3489-1038</orcidid></search><sort><creationdate>20240131</creationdate><title>A practical, tandem and protecting-group-free synthesis of (+)-rosmarinic acid and its analogues</title><author>Sun, Ying ; Fan, Peinan ; Zhao, Xiaolong ; Liu, Dan ; Ru, Yilin ; Bai, Yujun ; Bai, Yajun ; Zheng, Xiaohui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c306t-aa44b7ef71748e8c52ee2429d607d5423644e4aca78e37730ff22a6163a029313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>(+)-rosmarinic acid</topic><topic>Knoevenagel condensation</topic><topic>Protecting-group-free</topic><topic>Synthesis</topic><topic>Tandem reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Ying</creatorcontrib><creatorcontrib>Fan, Peinan</creatorcontrib><creatorcontrib>Zhao, Xiaolong</creatorcontrib><creatorcontrib>Liu, Dan</creatorcontrib><creatorcontrib>Ru, Yilin</creatorcontrib><creatorcontrib>Bai, Yujun</creatorcontrib><creatorcontrib>Bai, Yajun</creatorcontrib><creatorcontrib>Zheng, Xiaohui</creatorcontrib><collection>CrossRef</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Ying</au><au>Fan, Peinan</au><au>Zhao, Xiaolong</au><au>Liu, Dan</au><au>Ru, Yilin</au><au>Bai, Yujun</au><au>Bai, Yajun</au><au>Zheng, Xiaohui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A practical, tandem and protecting-group-free synthesis of (+)-rosmarinic acid and its analogues</atitle><jtitle>Tetrahedron letters</jtitle><date>2024-01-31</date><risdate>2024</risdate><volume>135</volume><spage>154879</spage><pages>154879-</pages><artnum>154879</artnum><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
A short, tandem and protecting-group-free total synthesis of (+)-rosmarinic acid and related ester derivatives from (+)-danshensu (or corresponding aryl lactic acid) and related hydroxybenzaldehydes in 54 %∼87 % overall yield is described. The key step is the Meldrum’s acid mediate tandem classical Knoevenagel condensation.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2023.154879</doi><orcidid>https://orcid.org/0000-0002-3489-1038</orcidid></addata></record> |
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source | ScienceDirect Journals |
subjects | (+)-rosmarinic acid Knoevenagel condensation Protecting-group-free Synthesis Tandem reaction |
title | A practical, tandem and protecting-group-free synthesis of (+)-rosmarinic acid and its analogues |
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