An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone
•A novel synthetic route of producing UDCA was developed from plant-source DHEA.•Most of the reactions have high conversions and overall yield to 35% for 8 steps. A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiand...
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| Veröffentlicht in: | Steroids 2021-08, Vol.172, p.108870-108870, Article 108870 |
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| creator | Chen, Wang Hu, Daihua Feng, Zili Liu, Zhaopeng |
| description | •A novel synthetic route of producing UDCA was developed from plant-source DHEA.•Most of the reactions have high conversions and overall yield to 35% for 8 steps.
A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiandrosterone (DHEA), with a Mistunobu reaction and regioselective allyl oxidationat as the key steps. The reaction conditions of the key allyl oxidation reaction were also investigated and optimized, including solvent, oxidant and reaction temperature. In this novel route for the preparation of UDCA, most of the reaction steps have high conversions and overall yield up to 35% for 8 steps. Since all starting materials are cost-effective, commercially available and effectively avoided the risk of animal derived raw materials, this promising synthetic route offers economical and efficient strategies for potential production of UDCA. |
| doi_str_mv | 10.1016/j.steroids.2021.108870 |
| format | Article |
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A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiandrosterone (DHEA), with a Mistunobu reaction and regioselective allyl oxidationat as the key steps. The reaction conditions of the key allyl oxidation reaction were also investigated and optimized, including solvent, oxidant and reaction temperature. In this novel route for the preparation of UDCA, most of the reaction steps have high conversions and overall yield up to 35% for 8 steps. Since all starting materials are cost-effective, commercially available and effectively avoided the risk of animal derived raw materials, this promising synthetic route offers economical and efficient strategies for potential production of UDCA.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2021.108870</identifier><identifier>PMID: 34038744</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Dehydroepiandrosterone ; Dehydroepiandrosterone - chemistry ; Oxidants - chemistry ; Oxidation-Reduction ; Solvents ; Synthesis ; Ursodeoxycholic acid ; Ursodeoxycholic Acid - chemical synthesis</subject><ispartof>Steroids, 2021-08, Vol.172, p.108870-108870, Article 108870</ispartof><rights>2021 Elsevier Inc.</rights><rights>Copyright © 2021 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-d504e0f9a90acefbcaa9a117cc674e27678e7738dea720d8a94576783763f9d43</citedby><cites>FETCH-LOGICAL-c368t-d504e0f9a90acefbcaa9a117cc674e27678e7738dea720d8a94576783763f9d43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2021.108870$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34038744$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Wang</creatorcontrib><creatorcontrib>Hu, Daihua</creatorcontrib><creatorcontrib>Feng, Zili</creatorcontrib><creatorcontrib>Liu, Zhaopeng</creatorcontrib><title>An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone</title><title>Steroids</title><addtitle>Steroids</addtitle><description>•A novel synthetic route of producing UDCA was developed from plant-source DHEA.•Most of the reactions have high conversions and overall yield to 35% for 8 steps.
A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiandrosterone (DHEA), with a Mistunobu reaction and regioselective allyl oxidationat as the key steps. The reaction conditions of the key allyl oxidation reaction were also investigated and optimized, including solvent, oxidant and reaction temperature. In this novel route for the preparation of UDCA, most of the reaction steps have high conversions and overall yield up to 35% for 8 steps. Since all starting materials are cost-effective, commercially available and effectively avoided the risk of animal derived raw materials, this promising synthetic route offers economical and efficient strategies for potential production of UDCA.</description><subject>Dehydroepiandrosterone</subject><subject>Dehydroepiandrosterone - chemistry</subject><subject>Oxidants - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Solvents</subject><subject>Synthesis</subject><subject>Ursodeoxycholic acid</subject><subject>Ursodeoxycholic Acid - chemical synthesis</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1OwzAQhC0EoqXwClWOXFLsOLGdG1XFrypxAYmb5dpr1VUaFzupyNuTkpYrp5FGszu7H0JTgmcEE3a3mcUGgncmzjKckd4UguMzNCaCi7QQjJ-jMca0TEkmPkfoKsYNxpjRMrtEI5pjKniej9HrvE7AWtCN20MSu7pZQ3Qx8TZpQ_QG_Hen175yOlHamcQGv00MrDsTPOycqnv9vaSGa3RhVRXh5qgT9PH48L54TpdvTy-L-TLVlIkmNQXOAdtSlVhpsCutVKkI4VoznkPGGRfAORUGFM-wEarMi4NJOaO2NDmdoNth7y74rxZiI7cuaqgqVYNvo8wKSikhhNE-yoao7q-MAazcBbdVoZMEywNHuZEnjvLAUQ4c-8HpsaNdbcH8jZ3A9YH7IQD9p3sHQUbtoNZgXOhhSuPdfx0_c1GI8w</recordid><startdate>202108</startdate><enddate>202108</enddate><creator>Chen, Wang</creator><creator>Hu, Daihua</creator><creator>Feng, Zili</creator><creator>Liu, Zhaopeng</creator><general>Elsevier Inc</general><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>202108</creationdate><title>An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone</title><author>Chen, Wang ; Hu, Daihua ; Feng, Zili ; Liu, Zhaopeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-d504e0f9a90acefbcaa9a117cc674e27678e7738dea720d8a94576783763f9d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Dehydroepiandrosterone</topic><topic>Dehydroepiandrosterone - chemistry</topic><topic>Oxidants - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Solvents</topic><topic>Synthesis</topic><topic>Ursodeoxycholic acid</topic><topic>Ursodeoxycholic Acid - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Wang</creatorcontrib><creatorcontrib>Hu, Daihua</creatorcontrib><creatorcontrib>Feng, Zili</creatorcontrib><creatorcontrib>Liu, Zhaopeng</creatorcontrib><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>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Wang</au><au>Hu, Daihua</au><au>Feng, Zili</au><au>Liu, Zhaopeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2021-08</date><risdate>2021</risdate><volume>172</volume><spage>108870</spage><epage>108870</epage><pages>108870-108870</pages><artnum>108870</artnum><issn>0039-128X</issn><eissn>1878-5867</eissn><abstract>•A novel synthetic route of producing UDCA was developed from plant-source DHEA.•Most of the reactions have high conversions and overall yield to 35% for 8 steps.
A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiandrosterone (DHEA), with a Mistunobu reaction and regioselective allyl oxidationat as the key steps. The reaction conditions of the key allyl oxidation reaction were also investigated and optimized, including solvent, oxidant and reaction temperature. In this novel route for the preparation of UDCA, most of the reaction steps have high conversions and overall yield up to 35% for 8 steps. Since all starting materials are cost-effective, commercially available and effectively avoided the risk of animal derived raw materials, this promising synthetic route offers economical and efficient strategies for potential production of UDCA.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>34038744</pmid><doi>10.1016/j.steroids.2021.108870</doi><tpages>1</tpages></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Dehydroepiandrosterone Dehydroepiandrosterone - chemistry Oxidants - chemistry Oxidation-Reduction Solvents Synthesis Ursodeoxycholic acid Ursodeoxycholic Acid - chemical synthesis |
| title | An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone |
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