Recent Advances in Prins Spirocyclization
The classical Prins cyclization has been one of the most intensively studied reactions during the last two decades, and it has found many applications in key steps of natural product syntheses, especially for products containing tetrahydropyran motifs and related structures in their core skeletons....
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| Veröffentlicht in: | European journal of organic chemistry 2017-10, Vol.2017 (37), p.5484-5496 |
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| container_issue | 37 |
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| container_title | European journal of organic chemistry |
| container_volume | 2017 |
| creator | Subba Reddy, B. V. Nair, Preethi Narayanan Antony, Aneesh Srivastava, Nikhil |
| description | The classical Prins cyclization has been one of the most intensively studied reactions during the last two decades, and it has found many applications in key steps of natural product syntheses, especially for products containing tetrahydropyran motifs and related structures in their core skeletons. The application of this reaction to the synthesis of spirocylic networks has made substantial progress recently. Spiro motifs are found in many natural products with promising biorelevance and are increasingly being incorporated in drug candidates. Further, various spirocyclic chiral ligands have shown promising efficiency in asymmetric synthesis. Here a compilation of recent spiroannulation reactions by Prins cyclization is presented, focusing on the scope and versatility of this method.
Application of the Prins cyclization to the synthesis of spirocylic networks has made substantial progress recently. Spiro motifs are found in many natural products with promising biorelevance and are increasingly being incorporated in drug candidates. Further, various spirocyclic chiral ligands have shown promise in asymmetric synthesis. |
| doi_str_mv | 10.1002/ejoc.201700633 |
| format | Article |
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Application of the Prins cyclization to the synthesis of spirocylic networks has made substantial progress recently. Spiro motifs are found in many natural products with promising biorelevance and are increasingly being incorporated in drug candidates. Further, various spirocyclic chiral ligands have shown promise in asymmetric synthesis.</description><subject>Asymmetric synthesis</subject><subject>Chemical synthesis</subject><subject>Cyclization</subject><subject>Natural products</subject><subject>Oxocarbenium ions</subject><subject>Oxygen heterocycles</subject><subject>Spiro compounds</subject><subject>Spirocyclization</subject><subject>Spirotetrahydropyran scaffolds</subject><subject>Tandem Prins cyclization</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkM1LxDAUxIMouK5ePRc8eWh9adq077iU9YuFFT_AW0jTFFJqW5OuUv96s1T06Om9w_xmhiHknEJEAeIr3fQqioFmAJyxA7KggBgCRzj0f8KSkCJ7PSYnzjUAgJzTBbl81Ep3Y7CqPmSntAtMFzxY07ngaTC2V5NqzZccTd-dkqNatk6f_dwleblePxe34WZ7c1esNqFiOWOhSpBlFGktEWqVoQaupY-SZYIpcKg0TbGEPIZc-tasTFVd-WI8l5kCRtmSXMy-g-3fd9qNoul3tvORgmKCvniax14VzSple-esrsVgzZu0k6Ag9nOI_Rzidw4P4Ax8mlZP_6jF-n5b_LHfg09hsA</recordid><startdate>20171010</startdate><enddate>20171010</enddate><creator>Subba Reddy, B. V.</creator><creator>Nair, Preethi Narayanan</creator><creator>Antony, Aneesh</creator><creator>Srivastava, Nikhil</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20171010</creationdate><title>Recent Advances in Prins Spirocyclization</title><author>Subba Reddy, B. V. ; Nair, Preethi Narayanan ; Antony, Aneesh ; Srivastava, Nikhil</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3833-c4937191fa90fc79e06ea661ab495060de159b08208a0023b5cfd19368a7c0313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Asymmetric synthesis</topic><topic>Chemical synthesis</topic><topic>Cyclization</topic><topic>Natural products</topic><topic>Oxocarbenium ions</topic><topic>Oxygen heterocycles</topic><topic>Spiro compounds</topic><topic>Spirocyclization</topic><topic>Spirotetrahydropyran scaffolds</topic><topic>Tandem Prins cyclization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Subba Reddy, B. V.</creatorcontrib><creatorcontrib>Nair, Preethi Narayanan</creatorcontrib><creatorcontrib>Antony, Aneesh</creatorcontrib><creatorcontrib>Srivastava, Nikhil</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Subba Reddy, B. V.</au><au>Nair, Preethi Narayanan</au><au>Antony, Aneesh</au><au>Srivastava, Nikhil</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Recent Advances in Prins Spirocyclization</atitle><jtitle>European journal of organic chemistry</jtitle><date>2017-10-10</date><risdate>2017</risdate><volume>2017</volume><issue>37</issue><spage>5484</spage><epage>5496</epage><pages>5484-5496</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The classical Prins cyclization has been one of the most intensively studied reactions during the last two decades, and it has found many applications in key steps of natural product syntheses, especially for products containing tetrahydropyran motifs and related structures in their core skeletons. The application of this reaction to the synthesis of spirocylic networks has made substantial progress recently. Spiro motifs are found in many natural products with promising biorelevance and are increasingly being incorporated in drug candidates. Further, various spirocyclic chiral ligands have shown promising efficiency in asymmetric synthesis. Here a compilation of recent spiroannulation reactions by Prins cyclization is presented, focusing on the scope and versatility of this method.
Application of the Prins cyclization to the synthesis of spirocylic networks has made substantial progress recently. Spiro motifs are found in many natural products with promising biorelevance and are increasingly being incorporated in drug candidates. Further, various spirocyclic chiral ligands have shown promise in asymmetric synthesis.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201700633</doi><tpages>13</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Asymmetric synthesis Chemical synthesis Cyclization Natural products Oxocarbenium ions Oxygen heterocycles Spiro compounds Spirocyclization Spirotetrahydropyran scaffolds Tandem Prins cyclization |
| title | Recent Advances in Prins Spirocyclization |
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