A Short Total Synthesis of the Marine Sponge Pyrrole-2-aminoimidazole Alkaloid (±)-Agelastatin A
Ring by ring: (±)‐Agelastatin A has been synthesized through the use of domino and one‐pot reactions while minimizing protecting group usage. The core was accessed through a stereoselective domino condensation/ring‐opening/4π‐conrotatory electrocyclization and elaborated using newly developed protoc...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2013-10, Vol.52 (41), p.10862-10866 |
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| container_issue | 41 |
| container_start_page | 10862 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 52 |
| creator | Duspara, Petar A. Batey, Robert A. |
| description | Ring by ring: (±)‐Agelastatin A has been synthesized through the use of domino and one‐pot reactions while minimizing protecting group usage. The core was accessed through a stereoselective domino condensation/ring‐opening/4π‐conrotatory electrocyclization and elaborated using newly developed protocols for urea and amide formation. Oxidation of an unprotected pre‐agelastatin A and an intramolecular aza‐Michael reaction completed the synthesis in only six steps. |
| doi_str_mv | 10.1002/anie.201304759 |
| format | Article |
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The core was accessed through a stereoselective domino condensation/ring‐opening/4π‐conrotatory electrocyclization and elaborated using newly developed protocols for urea and amide formation. Oxidation of an unprotected pre‐agelastatin A and an intramolecular aza‐Michael reaction completed the synthesis in only six steps.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201304759</identifier><identifier>PMID: 24038621</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Animals ; aza-Michael addition ; Cyclization ; domino reactions ; electrocyclization ; heterocycles ; Imidazoles - chemical synthesis ; Imidazoles - chemistry ; Oxazolidinones - chemical synthesis ; Oxazolidinones - chemistry ; Porifera - chemistry ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Stereoisomerism ; total synthesis</subject><ispartof>Angewandte Chemie International Edition, 2013-10, Vol.52 (41), p.10862-10866</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. 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Oxidation of an unprotected pre‐agelastatin A and an intramolecular aza‐Michael reaction completed the synthesis in only six steps.</description><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Animals</subject><subject>aza-Michael addition</subject><subject>Cyclization</subject><subject>domino reactions</subject><subject>electrocyclization</subject><subject>heterocycles</subject><subject>Imidazoles - chemical synthesis</subject><subject>Imidazoles - chemistry</subject><subject>Oxazolidinones - chemical synthesis</subject><subject>Oxazolidinones - chemistry</subject><subject>Porifera - chemistry</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Stereoisomerism</subject><subject>total synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtu1DAUhq2qqC2FLUvkZVl48CWOk2VU9aa2A9IMQmJjOfFJ69aJp3ZGdFix4YF4BR6FJyGjKaPuujpHR9__S-dD6B2jE0Yp_2h6BxNOmaCZkuUOOmCSMyKUErvjnglBVCHZPnqd0t3IFwXN99A-z6gocs4OUFPh2W2IA56HwXg8W_XDLSSXcGjxuOFrE10PeLYI_Q3gz6sYgwfCielcH1znrPkxHnDl740PzuKjP78_kOoGvEmDGVz_9-ev6g161Rqf4O3TPERfTk_mx-fk6tPZxXF1RZosK0tilCyYErbN68xYmyvLJWRlY0vR1LVUOQPaApVUlCBzWUspbMbrBkzNjSytOERHm95FDA9LSIPuXGrAe9NDWCY9qhHrxws-opMN2sSQUoRWL6LrTFxpRvVarF6L1VuxY-D9U_ey7sBu8f8mR6DcAN-dh9ULdbqaXpw8LyebrEsDPG6zJt7rXAkl9dfpmb68FpffiqnUc_EPMBeVag</recordid><startdate>20131004</startdate><enddate>20131004</enddate><creator>Duspara, Petar A.</creator><creator>Batey, Robert A.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20131004</creationdate><title>A Short Total Synthesis of the Marine Sponge Pyrrole-2-aminoimidazole Alkaloid (±)-Agelastatin A</title><author>Duspara, Petar A. ; Batey, Robert A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4499-a758173df6b4add67d25e49cd93cbb5761e0fe05039e565b553d42bceab2a59d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Animals</topic><topic>aza-Michael addition</topic><topic>Cyclization</topic><topic>domino reactions</topic><topic>electrocyclization</topic><topic>heterocycles</topic><topic>Imidazoles - chemical synthesis</topic><topic>Imidazoles - chemistry</topic><topic>Oxazolidinones - chemical synthesis</topic><topic>Oxazolidinones - chemistry</topic><topic>Porifera - chemistry</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Stereoisomerism</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Duspara, Petar A.</creatorcontrib><creatorcontrib>Batey, Robert A.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Duspara, Petar A.</au><au>Batey, Robert A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Short Total Synthesis of the Marine Sponge Pyrrole-2-aminoimidazole Alkaloid (±)-Agelastatin A</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. 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| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2013-10, Vol.52 (41), p.10862-10866 |
| issn | 1433-7851 1521-3773 |
| language | eng |
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| source | Wiley-Blackwell Journals; MEDLINE |
| subjects | Alkaloids - chemical synthesis Alkaloids - chemistry Animals aza-Michael addition Cyclization domino reactions electrocyclization heterocycles Imidazoles - chemical synthesis Imidazoles - chemistry Oxazolidinones - chemical synthesis Oxazolidinones - chemistry Porifera - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry Stereoisomerism total synthesis |
| title | A Short Total Synthesis of the Marine Sponge Pyrrole-2-aminoimidazole Alkaloid (±)-Agelastatin A |
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