Formation of 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones via ring-expansion of 4-ethynyl-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones. Total synthesis of methyl linderone
An in-depth study of the reactions of 4-(ethynyl)-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones with N-bromo- or N-iodosuccinimide, affording in most cases 2-halomethylene-4-cyclopentene-1,3-dione, is described. This reaction was used in a short total synthesis of methyl linderone. [Display omitted]
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| Veröffentlicht in: | Tetrahedron 2013-11, Vol.69 (44), p.9284-9293 |
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| container_issue | 44 |
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| container_title | Tetrahedron |
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| creator | Yin, Hong Dantale, Shubhada W. Akhmedov, Novruz G. Söderberg, Björn C.G. |
| description | An in-depth study of the reactions of 4-(ethynyl)-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones with N-bromo- or N-iodosuccinimide, affording in most cases 2-halomethylene-4-cyclopentene-1,3-dione, is described. This reaction was used in a short total synthesis of methyl linderone.
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| doi_str_mv | 10.1016/j.tet.2013.08.050 |
| format | Article |
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[Display omitted]</description><subject>2-Alkylidene-1,3-cyclopentendiones</subject><subject>Alkynylcyclobutenones</subject><subject>Formations</subject><subject>Methyl linderone</subject><subject>N-Halosuccinimide</subject><subject>Rearrangement</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kc1uHCEQhFGUSNk4eQDf5phDGDcM87PKKbJix5KlXJwzYobGy4qFDbCWJ2_otzKT2bNPqFVVH90qQi4Z1AxYd7WvM-aaA2tqGGpo4R3ZMNEJ2grWvScbAAFUAIeP5FNKewBgjDcb8nIT4kFlG3wVTMXpTrlwwLybHXqkgk7z5MIRfV5G9q2hulgxVcrrqxDPgSIIOqL_F_6erP-vP1lVResfKT4flU9nvqAL2s-ukHezjuF5prxA02lM2eZTRk35-udYBk8ZXWh19RCyclWafd5hsmlhrVtWznqNsbg-kw9GuYRfzu8F-XPz8-H6F73_fXt3_eOeTs22y9RszdAzjQz6sem4GDROY48oNFOiFeMwtooPZtuLQRTdjMJoUKCRYzO2RjUX5OvKPcZyLqYsDzZN6JzyGE5Jsl6Ibgu8HYqVrdYphpQiGnmM9qDiLBnIpTa5l6U2udQmYZCltpL5vmaw3PBkMco0WfQTahtxylIH-0b6Fe_ao7w</recordid><startdate>20131104</startdate><enddate>20131104</enddate><creator>Yin, Hong</creator><creator>Dantale, Shubhada W.</creator><creator>Akhmedov, Novruz G.</creator><creator>Söderberg, Björn C.G.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20131104</creationdate><title>Formation of 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones via ring-expansion of 4-ethynyl-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones. Total synthesis of methyl linderone</title><author>Yin, Hong ; Dantale, Shubhada W. ; Akhmedov, Novruz G. ; Söderberg, Björn C.G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-f9f871de107b36248decb7ee4d1a454b8b5a28f97484362fb4fd0a0de2e3b5fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>2-Alkylidene-1,3-cyclopentendiones</topic><topic>Alkynylcyclobutenones</topic><topic>Formations</topic><topic>Methyl linderone</topic><topic>N-Halosuccinimide</topic><topic>Rearrangement</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yin, Hong</creatorcontrib><creatorcontrib>Dantale, Shubhada W.</creatorcontrib><creatorcontrib>Akhmedov, Novruz G.</creatorcontrib><creatorcontrib>Söderberg, Björn C.G.</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>Yin, Hong</au><au>Dantale, Shubhada W.</au><au>Akhmedov, Novruz G.</au><au>Söderberg, Björn C.G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formation of 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones via ring-expansion of 4-ethynyl-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones. Total synthesis of methyl linderone</atitle><jtitle>Tetrahedron</jtitle><date>2013-11-04</date><risdate>2013</risdate><volume>69</volume><issue>44</issue><spage>9284</spage><epage>9293</epage><pages>9284-9293</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>An in-depth study of the reactions of 4-(ethynyl)-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones with N-bromo- or N-iodosuccinimide, affording in most cases 2-halomethylene-4-cyclopentene-1,3-dione, is described. This reaction was used in a short total synthesis of methyl linderone.
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| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2013-11, Vol.69 (44), p.9284-9293 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | 2-Alkylidene-1,3-cyclopentendiones Alkynylcyclobutenones Formations Methyl linderone N-Halosuccinimide Rearrangement Synthesis Tetrahedrons |
| title | Formation of 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones via ring-expansion of 4-ethynyl-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones. Total synthesis of methyl linderone |
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