Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition-Cyclization Strategy: Synthesis of (-)-Flustramine B
Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with α,β-unsaturated alde...
Gespeichert in:
| Veröffentlicht in: | Proceedings of the National Academy of Sciences - PNAS 2004-04, Vol.101 (15), p.5482-5487 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5487 |
|---|---|
| container_issue | 15 |
| container_start_page | 5482 |
| container_title | Proceedings of the National Academy of Sciences - PNAS |
| container_volume | 101 |
| creator | Austin, Joel F. Kim, Sung-Gon Sinz, Christopher J. Xiao, Wen-Jing David W. C. Mac Millan Halpern, Jack |
| description | Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with α,β-unsaturated aldehydes in the presence of imidazolidinone catalysts 1 and 8 provides pyrroloindoline adducts in high yield and excellent enantioselectivities. This transformation is successful for a wide range of tryptamine and α,β-unsaturated aldehyde substrates. This amine-catalyzed sequence has been extended to the enantioselective construction of furanoindoline frameworks. Application of this pyrroloindoline-forming reaction to natural product synthesis has been accomplished in the context of the enantioselective synthesis of (-)-flustramine B. |
| doi_str_mv | 10.1073/pnas.0308177101 |
| format | Article |
| fullrecord | <record><control><sourceid>jstor_proqu</sourceid><recordid>TN_cdi_proquest_journals_201405783</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><jstor_id>3371646</jstor_id><sourcerecordid>3371646</sourcerecordid><originalsourceid>FETCH-LOGICAL-c559t-2a90ee5b30802be9a396b6141c28d0a28f975d1b8d93fe5abb3c18acf133f253</originalsourceid><addsrcrecordid>eNp90cFu1DAQBuAIUdGlcOaCIOKAyiHtOI4TG4lDiVpAqlSk9m45jrP1ymtvbaciPAMPjdNddYEDJx_m-3-NNVn2CsEJggafbqwIJ4CBoqZBgJ5kCwQMFXXF4Gm2ACibglZldZg9D2EFAIxQeJYdIgJ18myR_Tq3wkbtgjJKRn2v8iu_FNZJEYWZopZ562yIfkxDZ3M35N8n751x2vbOaKtC3k25yFsRpOhVftb3epZFO0mjf4qH1HX0Iqrl9DG_nmy8VUGHuem4-FBcmDG1i3Vqyj-_yA4GYYJ6uXuPspuL85v2a3F59eVbe3ZZSEJYLErBQCnSpW9D2SkmMKu7GlVIlrQHUdKBNaRHHe0ZHhQRXYclokIOCOOhJPgo-7St3YzdWvVS2bSB4Ruv18JP3AnN_55YfcuX7p5j1lTAUv79Lu_d3ahC5GsdpDJGWOXGwBtES4rJDN_9A1du9DZ9jZeAKiANxQmdbpH0LgSvhsdFEPD5yHw-Mt8fOSXe_Ln_3u-umsDbHZiT-zqUCCcVLZM4_r_gw2hMVD9ioq-3dBWi848W4wbVVY1_A6-iyCM</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>201405783</pqid></control><display><type>article</type><title>Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition-Cyclization Strategy: Synthesis of (-)-Flustramine B</title><source>MEDLINE</source><source>JSTOR Archive Collection A-Z Listing</source><source>PubMed Central</source><source>Alma/SFX Local Collection</source><source>Free Full-Text Journals in Chemistry</source><creator>Austin, Joel F. ; Kim, Sung-Gon ; Sinz, Christopher J. ; Xiao, Wen-Jing ; David W. C. Mac Millan ; Halpern, Jack</creator><creatorcontrib>Austin, Joel F. ; Kim, Sung-Gon ; Sinz, Christopher J. ; Xiao, Wen-Jing ; David W. C. Mac Millan ; Halpern, Jack</creatorcontrib><description>Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with α,β-unsaturated aldehydes in the presence of imidazolidinone catalysts 1 and 8 provides pyrroloindoline adducts in high yield and excellent enantioselectivities. This transformation is successful for a wide range of tryptamine and α,β-unsaturated aldehyde substrates. This amine-catalyzed sequence has been extended to the enantioselective construction of furanoindoline frameworks. Application of this pyrroloindoline-forming reaction to natural product synthesis has been accomplished in the context of the enantioselective synthesis of (-)-flustramine B.</description><identifier>ISSN: 0027-8424</identifier><identifier>EISSN: 1091-6490</identifier><identifier>DOI: 10.1073/pnas.0308177101</identifier><identifier>PMID: 15067109</identifier><language>eng</language><publisher>United States: National Academy of Sciences</publisher><subject>Aldehydes ; Aldehydes - chemistry ; Alkaloids ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Amines ; Architecture ; Asymmetric Catalysis Special Feature Part I ; Carbon ; Catalysis ; Catalysts ; Cyclization ; From the Cover: ASYMMETRIC CATALYSIS SPECIAL FEATURE PART I ; Imidazoles - chemistry ; Indole Alkaloids ; Indoles ; Indoles - chemical synthesis ; Indoles - chemistry ; Organic chemistry ; Overman ; Pharmacology ; Physical Sciences ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Stereoisomerism ; Tetrahedrons ; Tryptamines - chemistry</subject><ispartof>Proceedings of the National Academy of Sciences - PNAS, 2004-04, Vol.101 (15), p.5482-5487</ispartof><rights>Copyright 1993/2004 The National Academy of Sciences of the United States of America</rights><rights>Copyright National Academy of Sciences Apr 13, 2004</rights><rights>Copyright © 2004, The National Academy of Sciences 2004</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c559t-2a90ee5b30802be9a396b6141c28d0a28f975d1b8d93fe5abb3c18acf133f253</citedby><cites>FETCH-LOGICAL-c559t-2a90ee5b30802be9a396b6141c28d0a28f975d1b8d93fe5abb3c18acf133f253</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://www.pnas.org/content/101/15.cover.gif</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/3371646$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/3371646$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,727,780,784,803,885,27923,27924,53790,53792,58016,58249</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15067109$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Austin, Joel F.</creatorcontrib><creatorcontrib>Kim, Sung-Gon</creatorcontrib><creatorcontrib>Sinz, Christopher J.</creatorcontrib><creatorcontrib>Xiao, Wen-Jing</creatorcontrib><creatorcontrib>David W. C. Mac Millan</creatorcontrib><creatorcontrib>Halpern, Jack</creatorcontrib><title>Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition-Cyclization Strategy: Synthesis of (-)-Flustramine B</title><title>Proceedings of the National Academy of Sciences - PNAS</title><addtitle>Proc Natl Acad Sci U S A</addtitle><description>Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with α,β-unsaturated aldehydes in the presence of imidazolidinone catalysts 1 and 8 provides pyrroloindoline adducts in high yield and excellent enantioselectivities. This transformation is successful for a wide range of tryptamine and α,β-unsaturated aldehyde substrates. This amine-catalyzed sequence has been extended to the enantioselective construction of furanoindoline frameworks. Application of this pyrroloindoline-forming reaction to natural product synthesis has been accomplished in the context of the enantioselective synthesis of (-)-flustramine B.</description><subject>Aldehydes</subject><subject>Aldehydes - chemistry</subject><subject>Alkaloids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Amines</subject><subject>Architecture</subject><subject>Asymmetric Catalysis Special Feature Part I</subject><subject>Carbon</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Cyclization</subject><subject>From the Cover: ASYMMETRIC CATALYSIS SPECIAL FEATURE PART I</subject><subject>Imidazoles - chemistry</subject><subject>Indole Alkaloids</subject><subject>Indoles</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Organic chemistry</subject><subject>Overman</subject><subject>Pharmacology</subject><subject>Physical Sciences</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Stereoisomerism</subject><subject>Tetrahedrons</subject><subject>Tryptamines - chemistry</subject><issn>0027-8424</issn><issn>1091-6490</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90cFu1DAQBuAIUdGlcOaCIOKAyiHtOI4TG4lDiVpAqlSk9m45jrP1ymtvbaciPAMPjdNddYEDJx_m-3-NNVn2CsEJggafbqwIJ4CBoqZBgJ5kCwQMFXXF4Gm2ACibglZldZg9D2EFAIxQeJYdIgJ18myR_Tq3wkbtgjJKRn2v8iu_FNZJEYWZopZ562yIfkxDZ3M35N8n751x2vbOaKtC3k25yFsRpOhVftb3epZFO0mjf4qH1HX0Iqrl9DG_nmy8VUGHuem4-FBcmDG1i3Vqyj-_yA4GYYJ6uXuPspuL85v2a3F59eVbe3ZZSEJYLErBQCnSpW9D2SkmMKu7GlVIlrQHUdKBNaRHHe0ZHhQRXYclokIOCOOhJPgo-7St3YzdWvVS2bSB4Ruv18JP3AnN_55YfcuX7p5j1lTAUv79Lu_d3ahC5GsdpDJGWOXGwBtES4rJDN_9A1du9DZ9jZeAKiANxQmdbpH0LgSvhsdFEPD5yHw-Mt8fOSXe_Ln_3u-umsDbHZiT-zqUCCcVLZM4_r_gw2hMVD9ioq-3dBWi848W4wbVVY1_A6-iyCM</recordid><startdate>20040413</startdate><enddate>20040413</enddate><creator>Austin, Joel F.</creator><creator>Kim, Sung-Gon</creator><creator>Sinz, Christopher J.</creator><creator>Xiao, Wen-Jing</creator><creator>David W. C. Mac Millan</creator><creator>Halpern, Jack</creator><general>National Academy of Sciences</general><general>National Acad Sciences</general><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>7QG</scope><scope>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7SN</scope><scope>7SS</scope><scope>7T5</scope><scope>7TK</scope><scope>7TM</scope><scope>7TO</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20040413</creationdate><title>Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition-Cyclization Strategy: Synthesis of (-)-Flustramine B</title><author>Austin, Joel F. ; Kim, Sung-Gon ; Sinz, Christopher J. ; Xiao, Wen-Jing ; David W. C. Mac Millan ; Halpern, Jack</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c559t-2a90ee5b30802be9a396b6141c28d0a28f975d1b8d93fe5abb3c18acf133f253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Aldehydes</topic><topic>Aldehydes - chemistry</topic><topic>Alkaloids</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Amines</topic><topic>Architecture</topic><topic>Asymmetric Catalysis Special Feature Part I</topic><topic>Carbon</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Cyclization</topic><topic>From the Cover: ASYMMETRIC CATALYSIS SPECIAL FEATURE PART I</topic><topic>Imidazoles - chemistry</topic><topic>Indole Alkaloids</topic><topic>Indoles</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Organic chemistry</topic><topic>Overman</topic><topic>Pharmacology</topic><topic>Physical Sciences</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Stereoisomerism</topic><topic>Tetrahedrons</topic><topic>Tryptamines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Austin, Joel F.</creatorcontrib><creatorcontrib>Kim, Sung-Gon</creatorcontrib><creatorcontrib>Sinz, Christopher J.</creatorcontrib><creatorcontrib>Xiao, Wen-Jing</creatorcontrib><creatorcontrib>David W. C. Mac Millan</creatorcontrib><creatorcontrib>Halpern, Jack</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Animal Behavior Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Immunology Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Oncogenes and Growth Factors Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Austin, Joel F.</au><au>Kim, Sung-Gon</au><au>Sinz, Christopher J.</au><au>Xiao, Wen-Jing</au><au>David W. C. Mac Millan</au><au>Halpern, Jack</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition-Cyclization Strategy: Synthesis of (-)-Flustramine B</atitle><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle><addtitle>Proc Natl Acad Sci U S A</addtitle><date>2004-04-13</date><risdate>2004</risdate><volume>101</volume><issue>15</issue><spage>5482</spage><epage>5487</epage><pages>5482-5487</pages><issn>0027-8424</issn><eissn>1091-6490</eissn><abstract>Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with α,β-unsaturated aldehydes in the presence of imidazolidinone catalysts 1 and 8 provides pyrroloindoline adducts in high yield and excellent enantioselectivities. This transformation is successful for a wide range of tryptamine and α,β-unsaturated aldehyde substrates. This amine-catalyzed sequence has been extended to the enantioselective construction of furanoindoline frameworks. Application of this pyrroloindoline-forming reaction to natural product synthesis has been accomplished in the context of the enantioselective synthesis of (-)-flustramine B.</abstract><cop>United States</cop><pub>National Academy of Sciences</pub><pmid>15067109</pmid><doi>10.1073/pnas.0308177101</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0027-8424 |
| ispartof | Proceedings of the National Academy of Sciences - PNAS, 2004-04, Vol.101 (15), p.5482-5487 |
| issn | 0027-8424 1091-6490 |
| language | eng |
| recordid | cdi_proquest_journals_201405783 |
| source | MEDLINE; JSTOR Archive Collection A-Z Listing; PubMed Central; Alma/SFX Local Collection; Free Full-Text Journals in Chemistry |
| subjects | Aldehydes Aldehydes - chemistry Alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry Amines Architecture Asymmetric Catalysis Special Feature Part I Carbon Catalysis Catalysts Cyclization From the Cover: ASYMMETRIC CATALYSIS SPECIAL FEATURE PART I Imidazoles - chemistry Indole Alkaloids Indoles Indoles - chemical synthesis Indoles - chemistry Organic chemistry Overman Pharmacology Physical Sciences Pyrroles - chemical synthesis Pyrroles - chemistry Stereoisomerism Tetrahedrons Tryptamines - chemistry |
| title | Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition-Cyclization Strategy: Synthesis of (-)-Flustramine B |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-11T08%3A44%3A00IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-jstor_proqu&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Enantioselective%20Organocatalytic%20Construction%20of%20Pyrroloindolines%20by%20a%20Cascade%20Addition-Cyclization%20Strategy:%20Synthesis%20of%20(-)-Flustramine%20B&rft.jtitle=Proceedings%20of%20the%20National%20Academy%20of%20Sciences%20-%20PNAS&rft.au=Austin,%20Joel%20F.&rft.date=2004-04-13&rft.volume=101&rft.issue=15&rft.spage=5482&rft.epage=5487&rft.pages=5482-5487&rft.issn=0027-8424&rft.eissn=1091-6490&rft_id=info:doi/10.1073/pnas.0308177101&rft_dat=%3Cjstor_proqu%3E3371646%3C/jstor_proqu%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=201405783&rft_id=info:pmid/15067109&rft_jstor_id=3371646&rfr_iscdi=true |