Substituted 2,2′-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles

We describe a new synthesis of the 3-chloro-(4′-methoxy)-2,2′-pyrrolylfuran segment (3) of (+)-roseophilin. The route exploits a isoxazoylpyrrole intermediate, wherein the isoxazole ring serves as a β-diketone equivalent and a directing group for palladium catalyzed chlorination of the attached pyrr...

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Veröffentlicht in:	Tetrahedron letters 2013-05, Vol.54 (21), p.2645-2647
Hauptverfasser:	Frederich, James H., Matsui, Jennifer K., Chang, Randy O., Harran, Patrick G.
Format:	Artikel
Sprache:	eng
Schlagworte:	3-Alkoxyfurans 3-Chloro-(4′-alkoxy)-2,2′-pyrrolylfuran C–H bond functionalization Isoxazole Prodiginine
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creator	Frederich, James H. Matsui, Jennifer K. Chang, Randy O. Harran, Patrick G.
description	We describe a new synthesis of the 3-chloro-(4′-methoxy)-2,2′-pyrrolylfuran segment (3) of (+)-roseophilin. The route exploits a isoxazoylpyrrole intermediate, wherein the isoxazole ring serves as a β-diketone equivalent and a directing group for palladium catalyzed chlorination of the attached pyrrole. Subsequent reduction of the N–O bond and acid promoted cyclization afford roseophilin segment 3b in five steps and 19% overall yield. This strategy was extended to the synthesis of 3-chloro-(4′-alkoxy)-2,2′-pyrrolylfurans (16a–c) and 4-alkoxy-2,2′-bipyrroles (20a–c), which are building blocks to synthesize bioactive prodiginine natural products and their congeners.
doi_str_mv	10.1016/j.tetlet.2013.03.034
format	Article
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The route exploits a isoxazoylpyrrole intermediate, wherein the isoxazole ring serves as a β-diketone equivalent and a directing group for palladium catalyzed chlorination of the attached pyrrole. Subsequent reduction of the N–O bond and acid promoted cyclization afford roseophilin segment 3b in five steps and 19% overall yield. This strategy was extended to the synthesis of 3-chloro-(4′-alkoxy)-2,2′-pyrrolylfurans (16a–c) and 4-alkoxy-2,2′-bipyrroles (20a–c), which are building blocks to synthesize bioactive prodiginine natural products and their congeners.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2013.03.034</identifier><identifier>PMID: 23814321</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>3-Alkoxyfurans ; 3-Chloro-(4′-alkoxy)-2,2′-pyrrolylfuran ; C–H bond functionalization ; Isoxazole ; Prodiginine</subject><ispartof>Tetrahedron letters, 2013-05, Vol.54 (21), p.2645-2647</ispartof><rights>2013 Elsevier Ltd</rights><rights>2011 Elsevier Ltd. All rights reserved. © 2013 Elsevier Ltd. 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This strategy was extended to the synthesis of 3-chloro-(4′-alkoxy)-2,2′-pyrrolylfurans (16a–c) and 4-alkoxy-2,2′-bipyrroles (20a–c), which are building blocks to synthesize bioactive prodiginine natural products and their congeners.</description><subject>3-Alkoxyfurans</subject><subject>3-Chloro-(4′-alkoxy)-2,2′-pyrrolylfuran</subject><subject>C–H bond functionalization</subject><subject>Isoxazole</subject><subject>Prodiginine</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9UctO3DAUtSoQTCl_gKosWTTD9QPH2SAhVAoSUhfQtWU718WjTDLYzojpqt_EJ_VLmmiAlg3WlSz7nnPu4xByRGFOgcqTxTxjbjHPGVA-hynEBzKjquIlP1V0h8wABJQCeL1PPqa0gPFIBXtkn3FFBWd0Ru5uB5tyyEPGpmBf2J_fT6UNq02MfYupMF1TbB-b1g_RdKlYB1OELmNcYhNMxiKk_tH8mhAvtE9k15s24eHzfUB-XH69u7gqb75_u744vymdkDyXBljjpfKUe--dtZZJaYVvpPHjZ8MMAK-sqowEU0PFa8Eqx7jx3ILzsuYH5Gyruxrs2I3DLkfT6lUMSxM3ujdBv8104V7_7Neay5oqxUeB42eB2D8MmLJehuSwbU2H_ZA0VUyeVlxWdISKLdTFPqWI_rUMBT0Zohd6a4ieDNEwhRhpn_9v8ZX04sC_GXBc1Dpg1MkF7Ny43Igu66YP71f4C0Djoz8</recordid><startdate>20130522</startdate><enddate>20130522</enddate><creator>Frederich, James H.</creator><creator>Matsui, Jennifer K.</creator><creator>Chang, Randy O.</creator><creator>Harran, Patrick G.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20130522</creationdate><title>Substituted 2,2′-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles</title><author>Frederich, James H. ; Matsui, Jennifer K. ; Chang, Randy O. ; Harran, Patrick G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c463t-a02df68f13fffcbbb266b4fd6af8f1d2a0037b87a60a90739427c23af3b0cf693</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>3-Alkoxyfurans</topic><topic>3-Chloro-(4′-alkoxy)-2,2′-pyrrolylfuran</topic><topic>C–H bond functionalization</topic><topic>Isoxazole</topic><topic>Prodiginine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Frederich, James H.</creatorcontrib><creatorcontrib>Matsui, Jennifer K.</creatorcontrib><creatorcontrib>Chang, Randy O.</creatorcontrib><creatorcontrib>Harran, Patrick G.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Frederich, James H.</au><au>Matsui, Jennifer K.</au><au>Chang, Randy O.</au><au>Harran, Patrick G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substituted 2,2′-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles</atitle><jtitle>Tetrahedron letters</jtitle><addtitle>Tetrahedron Lett</addtitle><date>2013-05-22</date><risdate>2013</risdate><volume>54</volume><issue>21</issue><spage>2645</spage><epage>2647</epage><pages>2645-2647</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>We describe a new synthesis of the 3-chloro-(4′-methoxy)-2,2′-pyrrolylfuran segment (3) of (+)-roseophilin. 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subjects	3-Alkoxyfurans 3-Chloro-(4′-alkoxy)-2,2′-pyrrolylfuran C–H bond functionalization Isoxazole Prodiginine
title	Substituted 2,2′-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles
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