The synthesis of the central tricyclic core of the isatisine A: harmonious orchestration of [metal]-catalyzed reactions in a sequence
Two sequential metal-catalyzed transformations, involving [In]-catalyzed Friedel–Crafts type addition of spiroaminol carbon to indole C3 followed by [Rh]-catalyzed dehydrogenative cyclization of the resulting γ-amino alcohol culminated in the construction of the central tricyclic core isatisine A. T...
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| Veröffentlicht in: | Tetrahedron 2014-01, Vol.70 (2), p.510-516 |
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| creator | Patel, Pitambar Narendraprasad Reddy, B. Ramana, C.V. |
| description | Two sequential metal-catalyzed transformations, involving [In]-catalyzed Friedel–Crafts type addition of spiroaminol carbon to indole C3 followed by [Rh]-catalyzed dehydrogenative cyclization of the resulting γ-amino alcohol culminated in the construction of the central tricyclic core isatisine A. The overall strategy employed three easily available starting compounds and delivered the complex tricyclic core in four steps—with all four steps being catalytic in nature.
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| doi_str_mv | 10.1016/j.tet.2013.11.026 |
| format | Article |
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[Display omitted]</description><subject>Carbon</subject><subject>Catalysis</subject><subject>Construction</subject><subject>Dehydrogenation</subject><subject>Dehydrogenative cyclization</subject><subject>Friedel–Crafts reaction</subject><subject>Indium chloride</subject><subject>Isatisine A</subject><subject>Rhodium</subject><subject>Spiro-3-indolinone</subject><subject>Strategy</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><subject>Transformations</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kM1LxDAQxYMouH78Ad5y9NI606ZpV08ifoHgZW8iITudslm6rSZRWO_-36asXj3NwLzfG94T4gwhR0B9sc4jx7wALHPEHAq9J2aotMoqhXpfzAAUZAoKOBRHIawBALEoZ-J7sWIZtkNccXBBjp1MmyQeore9jN7RlnpHkkbPf1cXbHTBDSyvL-XK-s04uPEjwZ6SSwKjG4dJ_LLhaPvXjGwa2y9upWdL0zVIN0grA79_8EB8Ig462wc-_Z3HYnF3u7h5yJ6e7x9vrp8yKkuIGRZUtFpXDXXEBdi6rMtijqpcgq6YVVt3usPKUt3W0PGc5tzMiWyzVA0tsTwW5zvbNz-mxyGajQvEfW8HTgEM1krppqo0JCnupOTHEDx35s27jfVbg2Cmxs3apMbN1LhBNKnxxFztGE4RPh17E8hN8VrnmaJpR_cP_QO0SYwW</recordid><startdate>20140114</startdate><enddate>20140114</enddate><creator>Patel, Pitambar</creator><creator>Narendraprasad Reddy, B.</creator><creator>Ramana, C.V.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20140114</creationdate><title>The synthesis of the central tricyclic core of the isatisine A: harmonious orchestration of [metal]-catalyzed reactions in a sequence</title><author>Patel, Pitambar ; Narendraprasad Reddy, B. ; Ramana, C.V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-12c2d6658cfce20a737329143b065ee4d7f6f15ac7d70fe9c9e89cca8b48cb13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Carbon</topic><topic>Catalysis</topic><topic>Construction</topic><topic>Dehydrogenation</topic><topic>Dehydrogenative cyclization</topic><topic>Friedel–Crafts reaction</topic><topic>Indium chloride</topic><topic>Isatisine A</topic><topic>Rhodium</topic><topic>Spiro-3-indolinone</topic><topic>Strategy</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Patel, Pitambar</creatorcontrib><creatorcontrib>Narendraprasad Reddy, B.</creatorcontrib><creatorcontrib>Ramana, C.V.</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Patel, Pitambar</au><au>Narendraprasad Reddy, B.</au><au>Ramana, C.V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The synthesis of the central tricyclic core of the isatisine A: harmonious orchestration of [metal]-catalyzed reactions in a sequence</atitle><jtitle>Tetrahedron</jtitle><date>2014-01-14</date><risdate>2014</risdate><volume>70</volume><issue>2</issue><spage>510</spage><epage>516</epage><pages>510-516</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>Two sequential metal-catalyzed transformations, involving [In]-catalyzed Friedel–Crafts type addition of spiroaminol carbon to indole C3 followed by [Rh]-catalyzed dehydrogenative cyclization of the resulting γ-amino alcohol culminated in the construction of the central tricyclic core isatisine A. The overall strategy employed three easily available starting compounds and delivered the complex tricyclic core in four steps—with all four steps being catalytic in nature.
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| ispartof | Tetrahedron, 2014-01, Vol.70 (2), p.510-516 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Carbon Catalysis Construction Dehydrogenation Dehydrogenative cyclization Friedel–Crafts reaction Indium chloride Isatisine A Rhodium Spiro-3-indolinone Strategy Synthesis Tetrahedrons Transformations |
| title | The synthesis of the central tricyclic core of the isatisine A: harmonious orchestration of [metal]-catalyzed reactions in a sequence |
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