A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)

A general route to oxoindolizino quinolines, such as nothapodytine A, mappicine, camptothecin, and several chemotherapeutic derivatives, is illustrated by the synthesis of the antiviral natural product from Nothapodytes foetida, mappicine ketone (R1=R4=H, R2=CH3, R3=COC2H5). A wide range of new camp...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2003-10, Vol.42 (41), p.5059-5061
Hauptverfasser: Raolji, Gajendra B., Garçon, Stéphanie, Greene, Andrew E., Kanazawa, Alice
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5061
container_issue 41
container_start_page 5059
container_title Angewandte Chemie International Edition
container_volume 42
creator Raolji, Gajendra B.
Garçon, Stéphanie
Greene, Andrew E.
Kanazawa, Alice
description A general route to oxoindolizino quinolines, such as nothapodytine A, mappicine, camptothecin, and several chemotherapeutic derivatives, is illustrated by the synthesis of the antiviral natural product from Nothapodytes foetida, mappicine ketone (R1=R4=H, R2=CH3, R3=COC2H5). A wide range of new camptothecinoids should now be readily available for biological testing.
doi_str_mv 10.1002/anie.200352094
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71333124</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71333124</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3794-61fd1a64328e4affb3fb95eec4abec81c0fc7b36626d10df897e07a7b972c3ff3</originalsourceid><addsrcrecordid>eNqFkEtv2zAQhIkiRfNorz0WPAXNQS6plUQpN9d1Y6OJjT6S9kZQ1BJmIouqKKF2fn1o2Eh762V3MfhmgB1C3nI24ozFH1RjcRQzBmnMiuQFOeFpzCMQAo7CnQBEIk_5MTn1_j7wec6yV-SYJ2mRZsBPiB3TG1cNterouG07p_SK9o4uN842lavto20c_TqEWdsG_SWdGmO1xaan37dNv0JvPXWG3qi2DXqD9Av2Lqz3C9evVOuqbb9TP168Ji-Nqj2-Oewzcvt5-mMyi66XV_PJ-DrSIIokyripuMoSiHNMlDElmLJIEXWiStQ518xoUUKWxVnFWWXyQiATSpSFiDUYA2fkfJ8bvvk9oO_l2nqNda0adIOXggMAj5MAjvag7pz3HRrZdnatuq3kTO7Klbty5XO5wfDukDyUa6z-4oc2A1DsgT-2xu1_4uR4MZ_-Gx7tvdb3uHn2qu5BZgJEKn8uruREzL7Nfn26kwU8AQcwlwM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71333124</pqid></control><display><type>article</type><title>A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)</title><source>MEDLINE</source><source>Wiley Online Library All Journals</source><creator>Raolji, Gajendra B. ; Garçon, Stéphanie ; Greene, Andrew E. ; Kanazawa, Alice</creator><creatorcontrib>Raolji, Gajendra B. ; Garçon, Stéphanie ; Greene, Andrew E. ; Kanazawa, Alice</creatorcontrib><description>A general route to oxoindolizino quinolines, such as nothapodytine A, mappicine, camptothecin, and several chemotherapeutic derivatives, is illustrated by the synthesis of the antiviral natural product from Nothapodytes foetida, mappicine ketone (R1=R4=H, R2=CH3, R3=COC2H5). A wide range of new camptothecinoids should now be readily available for biological testing.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200352094</identifier><identifier>PMID: 14595631</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Combinatorial Chemistry Techniques - methods ; cross-coupling ; cycloaddition ; Indolizines - chemical synthesis ; isomerization ; Models, Chemical ; Molecular Structure ; Quinolines - chemical synthesis ; rearrangement ; total synthesis</subject><ispartof>Angewandte Chemie International Edition, 2003-10, Vol.42 (41), p.5059-5061</ispartof><rights>Copyright © 2003 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3794-61fd1a64328e4affb3fb95eec4abec81c0fc7b36626d10df897e07a7b972c3ff3</citedby><cites>FETCH-LOGICAL-c3794-61fd1a64328e4affb3fb95eec4abec81c0fc7b36626d10df897e07a7b972c3ff3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.200352094$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14595631$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Raolji, Gajendra B.</creatorcontrib><creatorcontrib>Garçon, Stéphanie</creatorcontrib><creatorcontrib>Greene, Andrew E.</creatorcontrib><creatorcontrib>Kanazawa, Alice</creatorcontrib><title>A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)</title><title>Angewandte Chemie International Edition</title><addtitle>Angewandte Chemie International Edition</addtitle><description>A general route to oxoindolizino quinolines, such as nothapodytine A, mappicine, camptothecin, and several chemotherapeutic derivatives, is illustrated by the synthesis of the antiviral natural product from Nothapodytes foetida, mappicine ketone (R1=R4=H, R2=CH3, R3=COC2H5). A wide range of new camptothecinoids should now be readily available for biological testing.</description><subject>Combinatorial Chemistry Techniques - methods</subject><subject>cross-coupling</subject><subject>cycloaddition</subject><subject>Indolizines - chemical synthesis</subject><subject>isomerization</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Quinolines - chemical synthesis</subject><subject>rearrangement</subject><subject>total synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtv2zAQhIkiRfNorz0WPAXNQS6plUQpN9d1Y6OJjT6S9kZQ1BJmIouqKKF2fn1o2Eh762V3MfhmgB1C3nI24ozFH1RjcRQzBmnMiuQFOeFpzCMQAo7CnQBEIk_5MTn1_j7wec6yV-SYJ2mRZsBPiB3TG1cNterouG07p_SK9o4uN842lavto20c_TqEWdsG_SWdGmO1xaan37dNv0JvPXWG3qi2DXqD9Av2Lqz3C9evVOuqbb9TP168Ji-Nqj2-Oewzcvt5-mMyi66XV_PJ-DrSIIokyripuMoSiHNMlDElmLJIEXWiStQ518xoUUKWxVnFWWXyQiATSpSFiDUYA2fkfJ8bvvk9oO_l2nqNda0adIOXggMAj5MAjvag7pz3HRrZdnatuq3kTO7Klbty5XO5wfDukDyUa6z-4oc2A1DsgT-2xu1_4uR4MZ_-Gx7tvdb3uHn2qu5BZgJEKn8uruREzL7Nfn26kwU8AQcwlwM</recordid><startdate>20031027</startdate><enddate>20031027</enddate><creator>Raolji, Gajendra B.</creator><creator>Garçon, Stéphanie</creator><creator>Greene, Andrew E.</creator><creator>Kanazawa, Alice</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>20031027</creationdate><title>A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)</title><author>Raolji, Gajendra B. ; Garçon, Stéphanie ; Greene, Andrew E. ; Kanazawa, Alice</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3794-61fd1a64328e4affb3fb95eec4abec81c0fc7b36626d10df897e07a7b972c3ff3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Combinatorial Chemistry Techniques - methods</topic><topic>cross-coupling</topic><topic>cycloaddition</topic><topic>Indolizines - chemical synthesis</topic><topic>isomerization</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Quinolines - chemical synthesis</topic><topic>rearrangement</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Raolji, Gajendra B.</creatorcontrib><creatorcontrib>Garçon, Stéphanie</creatorcontrib><creatorcontrib>Greene, Andrew E.</creatorcontrib><creatorcontrib>Kanazawa, Alice</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>Raolji, Gajendra B.</au><au>Garçon, Stéphanie</au><au>Greene, Andrew E.</au><au>Kanazawa, Alice</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angewandte Chemie International Edition</addtitle><date>2003-10-27</date><risdate>2003</risdate><volume>42</volume><issue>41</issue><spage>5059</spage><epage>5061</epage><pages>5059-5061</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A general route to oxoindolizino quinolines, such as nothapodytine A, mappicine, camptothecin, and several chemotherapeutic derivatives, is illustrated by the synthesis of the antiviral natural product from Nothapodytes foetida, mappicine ketone (R1=R4=H, R2=CH3, R3=COC2H5). A wide range of new camptothecinoids should now be readily available for biological testing.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>14595631</pmid><doi>10.1002/anie.200352094</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie International Edition, 2003-10, Vol.42 (41), p.5059-5061
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_71333124
source MEDLINE; Wiley Online Library All Journals
subjects Combinatorial Chemistry Techniques - methods
cross-coupling
cycloaddition
Indolizines - chemical synthesis
isomerization
Models, Chemical
Molecular Structure
Quinolines - chemical synthesis
rearrangement
total synthesis
title A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-15T13%3A10%3A00IST&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=A%20Modular%20Approach%20to%20Oxoindolizino%20Quinolines:%20Efficient%20Synthesis%20of%20Mappicine%20Ketone%20(Nothapodytine%20B)&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Raolji,%20Gajendra%20B.&rft.date=2003-10-27&rft.volume=42&rft.issue=41&rft.spage=5059&rft.epage=5061&rft.pages=5059-5061&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.200352094&rft_dat=%3Cproquest_cross%3E71333124%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=71333124&rft_id=info:pmid/14595631&rfr_iscdi=true