Substituted 2,2a2-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles
We describe a new synthesis of the 3-chloro-(4a2-methoxy)-2,2a2-pyrrolylfuran segment (3) of (+)-roseophilin. The route exploits a isoxazoylpyrrole intermediate, wherein the isoxazole ring serves as a [beta]-diketone equivalent and a directing group for palladium catalyzed chlorination of the attach...
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Veröffentlicht in: | Tetrahedron letters 2013-05, Vol.54 (21), p.2645-2647 |
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description | We describe a new synthesis of the 3-chloro-(4a2-methoxy)-2,2a2-pyrrolylfuran segment (3) of (+)-roseophilin. The route exploits a isoxazoylpyrrole intermediate, wherein the isoxazole ring serves as a [beta]-diketone equivalent and a directing group for palladium catalyzed chlorination of the attached pyrrole. Subsequent reduction of the NaO 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-(4a2-alkoxy)-2,2a2-pyrrolylfurans (16aac) and 4-alkoxy-2,2a2-bipyrroles (20aac), which are building blocks to synthesize bioactive prodiginine natural products and their congeners. |
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The route exploits a isoxazoylpyrrole intermediate, wherein the isoxazole ring serves as a [beta]-diketone equivalent and a directing group for palladium catalyzed chlorination of the attached pyrrole. Subsequent reduction of the NaO 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-(4a2-alkoxy)-2,2a2-pyrrolylfurans (16aac) and 4-alkoxy-2,2a2-bipyrroles (20aac), which are building blocks to synthesize bioactive prodiginine natural products and their congeners.</description><identifier>ISSN: 0040-4039</identifier><language>eng</language><subject>Bonding ; Congeners ; Equivalence ; Rings (mathematics) ; Segments ; Strategy ; Synthesis ; Tetrahedrons</subject><ispartof>Tetrahedron letters, 2013-05, Vol.54 (21), p.2645-2647</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781</link.rule.ids></links><search><creatorcontrib>Frederich, James H</creatorcontrib><creatorcontrib>Matsui, Jennifer K</creatorcontrib><creatorcontrib>Chang, Randy O</creatorcontrib><creatorcontrib>Harran, Patrick G</creatorcontrib><title>Substituted 2,2a2-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles</title><title>Tetrahedron letters</title><description>We describe a new synthesis of the 3-chloro-(4a2-methoxy)-2,2a2-pyrrolylfuran segment (3) of (+)-roseophilin. 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title | Substituted 2,2a2-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles |
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