Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids
A facile one‐pot approach based on a thermally induced metal‐ and solvent‐free 5‐endo‐dig cyclization reaction of the amino propargylic alcohols in combination with Dess–Martin periodinane‐promoted oxidative dearomatization of 4,5,6,7‐tetrahydroindole intermediates provides an efficient and robust a...
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| Veröffentlicht in: | Chemistry : a European journal 2016-05, Vol.22 (21), p.7262-7267 |
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| creator | Andreev, Ivan A. Ratmanova, Nina K. Novoselov, Anton M. Belov, Dmitry S. Seregina, Irina F. Kurkin, Alexander V. |
| description | A facile one‐pot approach based on a thermally induced metal‐ and solvent‐free 5‐endo‐dig cyclization reaction of the amino propargylic alcohols in combination with Dess–Martin periodinane‐promoted oxidative dearomatization of 4,5,6,7‐tetrahydroindole intermediates provides an efficient and robust access to 5,6‐dihydro‐1H‐indol‐2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina‐ and Lycorine‐type alkaloids, namely (±)‐erysotramidine, (±)‐erysotrine, (±)‐erythravine, (±)‐γ‐lycorane, and abnormal erythrinanes (±)‐coccoline and (±)‐coccuvinine.
THIs means alkaloids: One‐pot technique including thermally induced cyclization of amino propargylic alcohols followed by Dess–Martin periodinane‐promoted oxidative dearomatization of intermediate 4,5,6,7‐tetrahydroindoles (THIs) grants a novel and distingue entry to 5,6‐dihydro‐1H‐indol‐2(4H)ones (see picture), which perfectly serve as universal key substrates in the formal total syntheses of numerous Erythrina and Lycorine alkaloids. |
| doi_str_mv | 10.1002/chem.201600273 |
| format | Article |
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THIs means alkaloids: One‐pot technique including thermally induced cyclization of amino propargylic alcohols followed by Dess–Martin periodinane‐promoted oxidative dearomatization of intermediate 4,5,6,7‐tetrahydroindoles (THIs) grants a novel and distingue entry to 5,6‐dihydro‐1H‐indol‐2(4H)ones (see picture), which perfectly serve as universal key substrates in the formal total syntheses of numerous Erythrina and Lycorine alkaloids.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201600273</identifier><identifier>PMID: 27076115</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>4,5,6,7-tetrahydroindoles ; 7-tetrahydroindoles ; Alcohols ; Alkaloids ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Amaryllidaceae Alkaloids - chemical synthesis ; Amaryllidaceae Alkaloids - chemistry ; Amplification ; Chemical reactions ; Chemistry ; Cyclization ; Erythrina - chemistry ; green chemistry ; Green Chemistry Technology - methods ; Hydrocarbons, Iodinated - chemical synthesis ; Hydrocarbons, Iodinated - chemistry ; Indoles - chemical synthesis ; Indoles - chemistry ; Oxidation-Reduction ; Phenanthridines - chemical synthesis ; Phenanthridines - chemistry ; Pictures ; Precursors ; Stereoisomerism ; Substrates ; Temperature ; thermally induced cyclization ; total synthesis ; Utilities</subject><ispartof>Chemistry : a European journal, 2016-05, Vol.22 (21), p.7262-7267</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0001-7602-7195 ; 0000-0002-7195-0535 ; 0000-0001-6142-9511</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201600273$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201600273$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27076115$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Andreev, Ivan A.</creatorcontrib><creatorcontrib>Ratmanova, Nina K.</creatorcontrib><creatorcontrib>Novoselov, Anton M.</creatorcontrib><creatorcontrib>Belov, Dmitry S.</creatorcontrib><creatorcontrib>Seregina, Irina F.</creatorcontrib><creatorcontrib>Kurkin, Alexander V.</creatorcontrib><title>Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A facile one‐pot approach based on a thermally induced metal‐ and solvent‐free 5‐endo‐dig cyclization reaction of the amino propargylic alcohols in combination with Dess–Martin periodinane‐promoted oxidative dearomatization of 4,5,6,7‐tetrahydroindole intermediates provides an efficient and robust access to 5,6‐dihydro‐1H‐indol‐2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina‐ and Lycorine‐type alkaloids, namely (±)‐erysotramidine, (±)‐erysotrine, (±)‐erythravine, (±)‐γ‐lycorane, and abnormal erythrinanes (±)‐coccoline and (±)‐coccuvinine.
THIs means alkaloids: One‐pot technique including thermally induced cyclization of amino propargylic alcohols followed by Dess–Martin periodinane‐promoted oxidative dearomatization of intermediate 4,5,6,7‐tetrahydroindoles (THIs) grants a novel and distingue entry to 5,6‐dihydro‐1H‐indol‐2(4H)ones (see picture), which perfectly serve as universal key substrates in the formal total syntheses of numerous Erythrina and Lycorine alkaloids.</description><subject>4,5,6,7-tetrahydroindoles</subject><subject>7-tetrahydroindoles</subject><subject>Alcohols</subject><subject>Alkaloids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Amaryllidaceae Alkaloids - chemical synthesis</subject><subject>Amaryllidaceae Alkaloids - chemistry</subject><subject>Amplification</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Erythrina - chemistry</subject><subject>green chemistry</subject><subject>Green Chemistry Technology - methods</subject><subject>Hydrocarbons, Iodinated - chemical synthesis</subject><subject>Hydrocarbons, Iodinated - chemistry</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Phenanthridines - chemical synthesis</subject><subject>Phenanthridines - chemistry</subject><subject>Pictures</subject><subject>Precursors</subject><subject>Stereoisomerism</subject><subject>Substrates</subject><subject>Temperature</subject><subject>thermally induced cyclization</subject><subject>total synthesis</subject><subject>Utilities</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFksFv0zAUxi0EYqVw5YgsceFQDzuO7YTbFroVqaMSFCFxsdz4ZfXmxMNJx8LfxB9JQksPXDhY9qf3-74n2w-hl4yeMkqTt-UW6tOEMjkIxR-hCRMJI1xJ8RhNaJ4qIgXPT9Cztr2hlOaS86foJFFUScbEBP1aPThrOncP-D2YGOrh_HNYocGhwulMzORMkTV00Wx7GwNhC-IaGzy0eLXpjGvA4k2Pr6AznmDTWPw5-HtoOnIRAfB6C7E2HgsCg4tYd42LvvSHHu_GOv4Udh3gLuB57LttdI35k7PsyzAIwGf-1vjgbPscPamMb-HFYZ-iLxfzdbEgy9Xlh-JsSa4F55yUWWVzyzeyTGhmlE0ls5ICNxTypFJZKhKrUp4KmySpTAU3SqWJFaBsRW2W8yl6s8-9i-H7DtpO164twXvTQNi1mmXDe3PJs_T_qMpyyjnlY-rrf9CbsIvNcJGRyiijcsicolcHarepweq76GoTe_33ywYg3wM_nIf-WGdUjwOhx4HQx4HQxWJ-dVSDl-y9ru3g4eg18VZLxZXQXz9eapEvskJ8o_qc_wZ91ra9</recordid><startdate>20160517</startdate><enddate>20160517</enddate><creator>Andreev, Ivan A.</creator><creator>Ratmanova, Nina K.</creator><creator>Novoselov, Anton M.</creator><creator>Belov, Dmitry S.</creator><creator>Seregina, Irina F.</creator><creator>Kurkin, Alexander V.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7602-7195</orcidid><orcidid>https://orcid.org/0000-0002-7195-0535</orcidid><orcidid>https://orcid.org/0000-0001-6142-9511</orcidid></search><sort><creationdate>20160517</creationdate><title>Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids</title><author>Andreev, Ivan A. ; Ratmanova, Nina K. ; Novoselov, Anton M. ; Belov, Dmitry S. ; Seregina, Irina F. ; Kurkin, Alexander V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g5333-c8fd9d3b6c208a7d461d60e3a0e92f78452d74345d2246453a7742d5e7df0d893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>4,5,6,7-tetrahydroindoles</topic><topic>7-tetrahydroindoles</topic><topic>Alcohols</topic><topic>Alkaloids</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Amaryllidaceae Alkaloids - chemical synthesis</topic><topic>Amaryllidaceae Alkaloids - chemistry</topic><topic>Amplification</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Erythrina - chemistry</topic><topic>green chemistry</topic><topic>Green Chemistry Technology - methods</topic><topic>Hydrocarbons, Iodinated - chemical synthesis</topic><topic>Hydrocarbons, Iodinated - chemistry</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Phenanthridines - chemical synthesis</topic><topic>Phenanthridines - chemistry</topic><topic>Pictures</topic><topic>Precursors</topic><topic>Stereoisomerism</topic><topic>Substrates</topic><topic>Temperature</topic><topic>thermally induced cyclization</topic><topic>total synthesis</topic><topic>Utilities</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Andreev, Ivan A.</creatorcontrib><creatorcontrib>Ratmanova, Nina K.</creatorcontrib><creatorcontrib>Novoselov, Anton M.</creatorcontrib><creatorcontrib>Belov, Dmitry S.</creatorcontrib><creatorcontrib>Seregina, Irina F.</creatorcontrib><creatorcontrib>Kurkin, Alexander V.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Andreev, Ivan A.</au><au>Ratmanova, Nina K.</au><au>Novoselov, Anton M.</au><au>Belov, Dmitry S.</au><au>Seregina, Irina F.</au><au>Kurkin, Alexander V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-05-17</date><risdate>2016</risdate><volume>22</volume><issue>21</issue><spage>7262</spage><epage>7267</epage><pages>7262-7267</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A facile one‐pot approach based on a thermally induced metal‐ and solvent‐free 5‐endo‐dig cyclization reaction of the amino propargylic alcohols in combination with Dess–Martin periodinane‐promoted oxidative dearomatization of 4,5,6,7‐tetrahydroindole intermediates provides an efficient and robust access to 5,6‐dihydro‐1H‐indol‐2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina‐ and Lycorine‐type alkaloids, namely (±)‐erysotramidine, (±)‐erysotrine, (±)‐erythravine, (±)‐γ‐lycorane, and abnormal erythrinanes (±)‐coccoline and (±)‐coccuvinine.
THIs means alkaloids: One‐pot technique including thermally induced cyclization of amino propargylic alcohols followed by Dess–Martin periodinane‐promoted oxidative dearomatization of intermediate 4,5,6,7‐tetrahydroindoles (THIs) grants a novel and distingue entry to 5,6‐dihydro‐1H‐indol‐2(4H)ones (see picture), which perfectly serve as universal key substrates in the formal total syntheses of numerous Erythrina and Lycorine alkaloids.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27076115</pmid><doi>10.1002/chem.201600273</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-7602-7195</orcidid><orcidid>https://orcid.org/0000-0002-7195-0535</orcidid><orcidid>https://orcid.org/0000-0001-6142-9511</orcidid></addata></record> |
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| subjects | 4,5,6,7-tetrahydroindoles 7-tetrahydroindoles Alcohols Alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry Amaryllidaceae Alkaloids - chemical synthesis Amaryllidaceae Alkaloids - chemistry Amplification Chemical reactions Chemistry Cyclization Erythrina - chemistry green chemistry Green Chemistry Technology - methods Hydrocarbons, Iodinated - chemical synthesis Hydrocarbons, Iodinated - chemistry Indoles - chemical synthesis Indoles - chemistry Oxidation-Reduction Phenanthridines - chemical synthesis Phenanthridines - chemistry Pictures Precursors Stereoisomerism Substrates Temperature thermally induced cyclization total synthesis Utilities |
| title | Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids |
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