A simple monoselective C-H oxygenation approach for the synthesis of ursane triterpenoids
Herein, we presented a simple approach for C-H oxidation in the C23 or/and C24 of ursane triterpenoids without any protection of a Δ 12,13 double bond. As a result, from commercial ursolic acid (UA), six naturally occurring ursane triterpenoids were synthesized in overall yields of 3.4% to 36.8%, wh...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-02, Vol.21 (7), p.1395-1398 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Mei, Wenyi Fan, Sisi Han, Yufei Shi, Cunjian Qiu, Lijie Shen, Yunheng Zhao, Zhenjiang Xu, Yufang Li, Honglin |
| description | Herein, we presented a simple approach for C-H oxidation in the C23 or/and C24 of ursane triterpenoids without any protection of a Δ
12,13
double bond. As a result, from commercial ursolic acid (UA), six naturally occurring ursane triterpenoids were synthesized in overall yields of 3.4% to 36.8%, which implied the importance of this approach for the derivation of natural products and their application in biological activity.
The total syntheses of six ursane triterpenoids have been realized from ursolic acid
via
a simple monoselective C-H oxygenation approach. |
| doi_str_mv | 10.1039/d3ob00016h |
| format | Article |
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12,13
double bond. As a result, from commercial ursolic acid (UA), six naturally occurring ursane triterpenoids were synthesized in overall yields of 3.4% to 36.8%, which implied the importance of this approach for the derivation of natural products and their application in biological activity.
The total syntheses of six ursane triterpenoids have been realized from ursolic acid
via
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12,13
double bond. As a result, from commercial ursolic acid (UA), six naturally occurring ursane triterpenoids were synthesized in overall yields of 3.4% to 36.8%, which implied the importance of this approach for the derivation of natural products and their application in biological activity.
The total syntheses of six ursane triterpenoids have been realized from ursolic acid
via
a simple monoselective C-H oxygenation approach.</description><subject>Biological activity</subject><subject>Biological Products - chemistry</subject><subject>Natural products</subject><subject>Oxidation</subject><subject>Oxygenation</subject><subject>Pentacyclic Triterpenes</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - pharmacology</subject><subject>Triterpenoids</subject><subject>Ursolic acid</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0c9LwzAUB_AgitPpxbsS8CJCNWnaJD3O-WPCYBc9eCpN-uoibVOTVtx_b3Rzgqf34H14vHyD0AklV5Sw7LpkVhFCKF_uoAOaCBGRlGW72z4mI3To_VsgmeDJPhoxzqVMRXyAXibYm6arATe2tR5q0L35ADyNZth-rl6hLXpjW1x0nbOFXuLKOtwvAftVG4o3HtsKD84XLeDemR5cB601pT9Ce1VRezje1DF6vr97ms6i-eLhcTqZRzrOeB9xXgiV6FQySTKpQqMoVaSCOOUyLVMpOVWlFoJpwUqiChbmEigXmiYKBBuji_XecOD7AL7PG-M11HW4yA4-j0V4K2WcxoGe_6NvdnBtuC4owVkqkkQGdblW2lnvHVR550xTuFVOSf4deH7LFjc_gc8CPtusHFQD5Zb-JhzA6Ro4r7fTvx9jXznShJQ</recordid><startdate>20230215</startdate><enddate>20230215</enddate><creator>Mei, Wenyi</creator><creator>Fan, Sisi</creator><creator>Han, Yufei</creator><creator>Shi, Cunjian</creator><creator>Qiu, Lijie</creator><creator>Shen, Yunheng</creator><creator>Zhao, Zhenjiang</creator><creator>Xu, Yufang</creator><creator>Li, Honglin</creator><general>Royal Society of Chemistry</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>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2270-1900</orcidid><orcidid>https://orcid.org/0000-0002-2075-2969</orcidid><orcidid>https://orcid.org/0000-0003-4946-4722</orcidid></search><sort><creationdate>20230215</creationdate><title>A simple monoselective C-H oxygenation approach for the synthesis of ursane triterpenoids</title><author>Mei, Wenyi ; Fan, Sisi ; Han, Yufei ; Shi, Cunjian ; Qiu, Lijie ; Shen, Yunheng ; Zhao, Zhenjiang ; Xu, Yufang ; Li, Honglin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-66a7b4c5838098bc58b11b0fe25685d58861bdc773c73d0ba3b118e167c14be73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Biological activity</topic><topic>Biological Products - chemistry</topic><topic>Natural products</topic><topic>Oxidation</topic><topic>Oxygenation</topic><topic>Pentacyclic Triterpenes</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - pharmacology</topic><topic>Triterpenoids</topic><topic>Ursolic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mei, Wenyi</creatorcontrib><creatorcontrib>Fan, Sisi</creatorcontrib><creatorcontrib>Han, Yufei</creatorcontrib><creatorcontrib>Shi, Cunjian</creatorcontrib><creatorcontrib>Qiu, Lijie</creatorcontrib><creatorcontrib>Shen, Yunheng</creatorcontrib><creatorcontrib>Zhao, Zhenjiang</creatorcontrib><creatorcontrib>Xu, Yufang</creatorcontrib><creatorcontrib>Li, Honglin</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mei, Wenyi</au><au>Fan, Sisi</au><au>Han, Yufei</au><au>Shi, Cunjian</au><au>Qiu, Lijie</au><au>Shen, Yunheng</au><au>Zhao, Zhenjiang</au><au>Xu, Yufang</au><au>Li, Honglin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A simple monoselective C-H oxygenation approach for the synthesis of ursane triterpenoids</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2023-02-15</date><risdate>2023</risdate><volume>21</volume><issue>7</issue><spage>1395</spage><epage>1398</epage><pages>1395-1398</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Herein, we presented a simple approach for C-H oxidation in the C23 or/and C24 of ursane triterpenoids without any protection of a Δ
12,13
double bond. As a result, from commercial ursolic acid (UA), six naturally occurring ursane triterpenoids were synthesized in overall yields of 3.4% to 36.8%, which implied the importance of this approach for the derivation of natural products and their application in biological activity.
The total syntheses of six ursane triterpenoids have been realized from ursolic acid
via
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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2023-02, Vol.21 (7), p.1395-1398 |
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| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Biological activity Biological Products - chemistry Natural products Oxidation Oxygenation Pentacyclic Triterpenes Triterpenes - chemistry Triterpenes - pharmacology Triterpenoids Ursolic acid |
| title | A simple monoselective C-H oxygenation approach for the synthesis of ursane triterpenoids |
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