Synthetic Study of Natural Metabolites Containing a Benzo[ c ]oxepine Skeleton: Heterocornol C and D
A versatile strategy for the enantioselective synthesis of a benzo[ ]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki-Miyaura cross-coupling re...
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| Veröffentlicht in: | International journal of molecular sciences 2023-06, Vol.24 (12), p.10331 |
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| container_title | International journal of molecular sciences |
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| creator | Gettler, Ján Čarný, Tomáš Markovič, Martin Koóš, Peter Samoľová, Erika Moncoľ, Ján Gracza, Tibor |
| description | A versatile strategy for the enantioselective synthesis of a benzo[
]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki-Miyaura cross-coupling reaction for the installation of the double bond and Katsuki-Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D (
) were achieved. Four stereoisomers,
,
-
,
and
-
, of this natural polyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone. |
| doi_str_mv | 10.3390/ijms241210331 |
| format | Article |
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]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki-Miyaura cross-coupling reaction for the installation of the double bond and Katsuki-Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D (
) were achieved. Four stereoisomers,
,
-
,
and
-
, of this natural polyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.</description><identifier>ISSN: 1422-0067</identifier><identifier>ISSN: 1661-6596</identifier><identifier>EISSN: 1422-0067</identifier><identifier>DOI: 10.3390/ijms241210331</identifier><identifier>PMID: 37373480</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Absolute configuration ; Analysis ; Benzoic acid ; Chemical properties ; Chemical reactions ; Configurations ; Cross coupling ; Enantiomers ; Metabolites ; Metathesis ; Olefins ; Organic acids ; Organic compounds ; Plant metabolites ; Potassium ; Scientific equipment and supplies industry ; Secondary metabolites ; Single crystals ; Stereoisomerism ; Stereoisomers ; Synthesis ; X ray analysis</subject><ispartof>International journal of molecular sciences, 2023-06, Vol.24 (12), p.10331</ispartof><rights>COPYRIGHT 2023 MDPI AG</rights><rights>2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2023 by the authors. 2023</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c483t-457685eee232a745beda012e3c502c45fa484fc4ca55bb88be01fb6e78fb8d123</citedby><cites>FETCH-LOGICAL-c483t-457685eee232a745beda012e3c502c45fa484fc4ca55bb88be01fb6e78fb8d123</cites><orcidid>0000-0003-3091-7699 ; 0000-0002-7667-0663 ; 0000-0003-2153-9753</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10299168/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10299168/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37373480$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gettler, Ján</creatorcontrib><creatorcontrib>Čarný, Tomáš</creatorcontrib><creatorcontrib>Markovič, Martin</creatorcontrib><creatorcontrib>Koóš, Peter</creatorcontrib><creatorcontrib>Samoľová, Erika</creatorcontrib><creatorcontrib>Moncoľ, Ján</creatorcontrib><creatorcontrib>Gracza, Tibor</creatorcontrib><title>Synthetic Study of Natural Metabolites Containing a Benzo[ c ]oxepine Skeleton: Heterocornol C and D</title><title>International journal of molecular sciences</title><addtitle>Int J Mol Sci</addtitle><description>A versatile strategy for the enantioselective synthesis of a benzo[
]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki-Miyaura cross-coupling reaction for the installation of the double bond and Katsuki-Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D (
) were achieved. Four stereoisomers,
,
-
,
and
-
, of this natural polyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.</description><subject>Absolute configuration</subject><subject>Analysis</subject><subject>Benzoic acid</subject><subject>Chemical properties</subject><subject>Chemical reactions</subject><subject>Configurations</subject><subject>Cross coupling</subject><subject>Enantiomers</subject><subject>Metabolites</subject><subject>Metathesis</subject><subject>Olefins</subject><subject>Organic acids</subject><subject>Organic compounds</subject><subject>Plant metabolites</subject><subject>Potassium</subject><subject>Scientific equipment and supplies industry</subject><subject>Secondary metabolites</subject><subject>Single crystals</subject><subject>Stereoisomerism</subject><subject>Stereoisomers</subject><subject>Synthesis</subject><subject>X ray analysis</subject><issn>1422-0067</issn><issn>1661-6596</issn><issn>1422-0067</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>8G5</sourceid><sourceid>BENPR</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNptks1v1DAQxSMEoqVw5IosceGS4s_E4YLKQilSC4eFE0KW44y3XhJ7azuI5a-vq5a2i9AcbNm_eeNnvap6TvAhYx1-7dZTopxQghkjD6p9wimtMW7ah_f2e9WTlNYYU0ZF97jaY20pLvF-NSy3Pp9DdgYt8zxsUbDos85z1CM6g6z7MLoMCS2Cz9p551dIo3fg_4TvyKAf4TdsnAe0_Akj5ODfoBPIEIMJ0YcRLZD2A3r_tHpk9Zjg2c16UH07_vB1cVKffvn4aXF0WhsuWa65aBspAKA8U7dc9DBoTCgwIzA1XFjNJbeGGy1E30vZAya2b6CVtpcDoeygenutu5n7CQYDPhcfahPdpONWBe3U7o1352oVfimCadeRRhaFVzcKMVzMkLKaXDIwjtpDmJOikuGm4bQTBX35D7oOc_TFX6FoJxlvCLujVnoE5bwNZbC5ElVHrZCMNB3tCnX4H6rUAJMzwYN15Xynob5uMDGkFMHemiRYXeVC7eSi8C_u_8wt_TcI7BLmtbLl</recordid><startdate>20230619</startdate><enddate>20230619</enddate><creator>Gettler, Ján</creator><creator>Čarný, Tomáš</creator><creator>Markovič, Martin</creator><creator>Koóš, Peter</creator><creator>Samoľová, Erika</creator><creator>Moncoľ, Ján</creator><creator>Gracza, Tibor</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-3091-7699</orcidid><orcidid>https://orcid.org/0000-0002-7667-0663</orcidid><orcidid>https://orcid.org/0000-0003-2153-9753</orcidid></search><sort><creationdate>20230619</creationdate><title>Synthetic Study of Natural Metabolites Containing a Benzo[ c ]oxepine Skeleton: Heterocornol C and D</title><author>Gettler, Ján ; Čarný, Tomáš ; Markovič, Martin ; Koóš, Peter ; Samoľová, Erika ; Moncoľ, Ján ; Gracza, Tibor</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c483t-457685eee232a745beda012e3c502c45fa484fc4ca55bb88be01fb6e78fb8d123</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Absolute configuration</topic><topic>Analysis</topic><topic>Benzoic acid</topic><topic>Chemical properties</topic><topic>Chemical reactions</topic><topic>Configurations</topic><topic>Cross coupling</topic><topic>Enantiomers</topic><topic>Metabolites</topic><topic>Metathesis</topic><topic>Olefins</topic><topic>Organic acids</topic><topic>Organic compounds</topic><topic>Plant metabolites</topic><topic>Potassium</topic><topic>Scientific equipment and supplies industry</topic><topic>Secondary metabolites</topic><topic>Single crystals</topic><topic>Stereoisomerism</topic><topic>Stereoisomers</topic><topic>Synthesis</topic><topic>X ray analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gettler, Ján</creatorcontrib><creatorcontrib>Čarný, Tomáš</creatorcontrib><creatorcontrib>Markovič, Martin</creatorcontrib><creatorcontrib>Koóš, Peter</creatorcontrib><creatorcontrib>Samoľová, Erika</creatorcontrib><creatorcontrib>Moncoľ, Ján</creatorcontrib><creatorcontrib>Gracza, Tibor</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Research Library (Corporate)</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>International journal of molecular sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gettler, Ján</au><au>Čarný, Tomáš</au><au>Markovič, Martin</au><au>Koóš, Peter</au><au>Samoľová, Erika</au><au>Moncoľ, Ján</au><au>Gracza, Tibor</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthetic Study of Natural Metabolites Containing a Benzo[ c ]oxepine Skeleton: Heterocornol C and D</atitle><jtitle>International journal of molecular sciences</jtitle><addtitle>Int J Mol Sci</addtitle><date>2023-06-19</date><risdate>2023</risdate><volume>24</volume><issue>12</issue><spage>10331</spage><pages>10331-</pages><issn>1422-0067</issn><issn>1661-6596</issn><eissn>1422-0067</eissn><abstract>A versatile strategy for the enantioselective synthesis of a benzo[
]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki-Miyaura cross-coupling reaction for the installation of the double bond and Katsuki-Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D (
) were achieved. Four stereoisomers,
,
-
,
and
-
, of this natural polyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>37373480</pmid><doi>10.3390/ijms241210331</doi><orcidid>https://orcid.org/0000-0003-3091-7699</orcidid><orcidid>https://orcid.org/0000-0002-7667-0663</orcidid><orcidid>https://orcid.org/0000-0003-2153-9753</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | International journal of molecular sciences, 2023-06, Vol.24 (12), p.10331 |
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| language | eng |
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| source | MDPI - Multidisciplinary Digital Publishing Institute; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central |
| subjects | Absolute configuration Analysis Benzoic acid Chemical properties Chemical reactions Configurations Cross coupling Enantiomers Metabolites Metathesis Olefins Organic acids Organic compounds Plant metabolites Potassium Scientific equipment and supplies industry Secondary metabolites Single crystals Stereoisomerism Stereoisomers Synthesis X ray analysis |
| title | Synthetic Study of Natural Metabolites Containing a Benzo[ c ]oxepine Skeleton: Heterocornol C and D |
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