Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence

Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence

A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8−C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offer...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2002-10, Vol.4 (22), p.3847-3850
Hauptverfasser: Durand-Reville, Thomas, Gobbi, Luca B, Gray, Brian Lawrence, Ley, Steven V, Scott, James S
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3850
container_issue 22
container_start_page 3847
container_title Organic letters
container_volume 4
creator Durand-Reville, Thomas
Gobbi, Luca B
Gray, Brian Lawrence
Ley, Steven V
Scott, James S
description A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8−C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin.
doi_str_mv 10.1021/ol0201557
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72849526</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72849526</sourcerecordid><originalsourceid>FETCH-LOGICAL-a377t-9caae9fc169a85b3c63b0f7f5be56b08a39d287831878800dcc92f1e68c5b67f3</originalsourceid><addsrcrecordid>eNpt0MtKAzEUBuAgiq2XhS8g2Si4qCaZZjJZSvEGgtDqejiTnrGpaaYmqdA-vZEW3bhJQvjyH_ITcsbZNWeC33SOCcalVHukz6UoBopJsf97LlmPHMU4Z4znG31IelxIrYdq2Cfu0b7P3JpO0KFJ9gvpnU9hTVNH0wzp7QamNoCZJevp5COj1Hn6ZYECHTmwET0dI4QA_h0X6NPNOD8w4OhobZzdQLLZT_Bzhd7gCTlowUU83e3H5O3-7nX0OHh-eXga3T4PoFAqDbQBQN0aXmqoZFOYsmhYq1rZoCwbVkGhp6JSVcHzUjE2NUaLlmNZGdmUqi2OyeU2dxm6PDmmemGjQefAY7eKtRLVUEtRZni1hSZ0MQZs62WwCwjrmrP6p9r6t9psz3ehq2aB0z-56zKDiy0AE-t5two-__GfoG9zDoCI</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72849526</pqid></control><display><type>article</type><title>Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence</title><source>ACS Publications</source><creator>Durand-Reville, Thomas ; Gobbi, Luca B ; Gray, Brian Lawrence ; Ley, Steven V ; Scott, James S</creator><creatorcontrib>Durand-Reville, Thomas ; Gobbi, Luca B ; Gray, Brian Lawrence ; Ley, Steven V ; Scott, James S</creatorcontrib><description>A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8−C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0201557</identifier><identifier>PMID: 12599474</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2002-10, Vol.4 (22), p.3847-3850</ispartof><rights>Copyright © 2002 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-9caae9fc169a85b3c63b0f7f5be56b08a39d287831878800dcc92f1e68c5b67f3</citedby><cites>FETCH-LOGICAL-a377t-9caae9fc169a85b3c63b0f7f5be56b08a39d287831878800dcc92f1e68c5b67f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol0201557$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol0201557$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12599474$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Durand-Reville, Thomas</creatorcontrib><creatorcontrib>Gobbi, Luca B</creatorcontrib><creatorcontrib>Gray, Brian Lawrence</creatorcontrib><creatorcontrib>Ley, Steven V</creatorcontrib><creatorcontrib>Scott, James S</creatorcontrib><title>Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8−C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNpt0MtKAzEUBuAgiq2XhS8g2Si4qCaZZjJZSvEGgtDqejiTnrGpaaYmqdA-vZEW3bhJQvjyH_ITcsbZNWeC33SOCcalVHukz6UoBopJsf97LlmPHMU4Z4znG31IelxIrYdq2Cfu0b7P3JpO0KFJ9gvpnU9hTVNH0wzp7QamNoCZJevp5COj1Hn6ZYECHTmwET0dI4QA_h0X6NPNOD8w4OhobZzdQLLZT_Bzhd7gCTlowUU83e3H5O3-7nX0OHh-eXga3T4PoFAqDbQBQN0aXmqoZFOYsmhYq1rZoCwbVkGhp6JSVcHzUjE2NUaLlmNZGdmUqi2OyeU2dxm6PDmmemGjQefAY7eKtRLVUEtRZni1hSZ0MQZs62WwCwjrmrP6p9r6t9psz3ehq2aB0z-56zKDiy0AE-t5two-__GfoG9zDoCI</recordid><startdate>20021031</startdate><enddate>20021031</enddate><creator>Durand-Reville, Thomas</creator><creator>Gobbi, Luca B</creator><creator>Gray, Brian Lawrence</creator><creator>Ley, Steven V</creator><creator>Scott, James S</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20021031</creationdate><title>Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence</title><author>Durand-Reville, Thomas ; Gobbi, Luca B ; Gray, Brian Lawrence ; Ley, Steven V ; Scott, James S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-9caae9fc169a85b3c63b0f7f5be56b08a39d287831878800dcc92f1e68c5b67f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Durand-Reville, Thomas</creatorcontrib><creatorcontrib>Gobbi, Luca B</creatorcontrib><creatorcontrib>Gray, Brian Lawrence</creatorcontrib><creatorcontrib>Ley, Steven V</creatorcontrib><creatorcontrib>Scott, James S</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Durand-Reville, Thomas</au><au>Gobbi, Luca B</au><au>Gray, Brian Lawrence</au><au>Ley, Steven V</au><au>Scott, James S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2002-10-31</date><risdate>2002</risdate><volume>4</volume><issue>22</issue><spage>3847</spage><epage>3850</epage><pages>3847-3850</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8−C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12599474</pmid><doi>10.1021/ol0201557</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2002-10, Vol.4 (22), p.3847-3850
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_72849526
source ACS Publications
title Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-13T11%3A38%3A56IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Highly%20Selective%20Entry%20to%20the%20Azadirachtin%20Skeleton%20via%20a%20Claisen%20Rearrangement/Radical%20Cyclization%20Sequence&rft.jtitle=Organic%20letters&rft.au=Durand-Reville,%20Thomas&rft.date=2002-10-31&rft.volume=4&rft.issue=22&rft.spage=3847&rft.epage=3850&rft.pages=3847-3850&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol0201557&rft_dat=%3Cproquest_cross%3E72849526%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=72849526&rft_id=info:pmid/12599474&rfr_iscdi=true