Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin

[structure: see text] The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2006-01, Vol.8 (1), p.135-138
Hauptverfasser: Frenzel, Thomas, Brünjes, Marco, Quitschalle, Monika, Kirschning, Andreas
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 138
container_issue 1
container_start_page 135
container_title Organic letters
container_volume 8
creator Frenzel, Thomas
Brünjes, Marco
Quitschalle, Monika
Kirschning, Andreas
description [structure: see text] The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.
doi_str_mv 10.1021/ol052588q
format Article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_67600018</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67600018</sourcerecordid><originalsourceid>FETCH-LOGICAL-j275t-ae64f8f3b90546ffdaf73edf0a4fb599ba9afb786034c22d504450e2a9447bbd3</originalsourceid><addsrcrecordid>eNo1jz1PwzAQhj2AaCkM_AHUiS1w_nZGVD6lCgZgjuzkLFwlcRsnQ_49RpTp7t57dO-9hFxRuKXA6F1sQTJpzOGELKlkvNCgYEHOU9oB0KyUZ2RBFTdUGrUkDx9zP35jCmkd_Tp367fC1jjObT2nEW0XesxyiJin4ZdJWMdiP0Tbp7wdYx36C3LqbZvw8lhX5Ovp8XPzUmzfn18399tix7QcC4tKeOO5K0EK5X1jvebYeLDCO1mWzpbWO20UcFEz1kgQQgIyWwqhnWv4itz83c32hyl_VHUh1di2tsc4pUppBTmkyeD1EZxch021H0Jnh7n6z81_ALXpWJA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67600018</pqid></control><display><type>article</type><title>Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Frenzel, Thomas ; Brünjes, Marco ; Quitschalle, Monika ; Kirschning, Andreas</creator><creatorcontrib>Frenzel, Thomas ; Brünjes, Marco ; Quitschalle, Monika ; Kirschning, Andreas</creatorcontrib><description>[structure: see text] The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.</description><identifier>ISSN: 1523-7060</identifier><identifier>DOI: 10.1021/ol052588q</identifier><identifier>PMID: 16381586</identifier><language>eng</language><publisher>United States</publisher><subject>Cysteamine - analogs &amp; derivatives ; Cysteamine - chemistry ; Esters ; Maytansine - analogs &amp; derivatives ; Maytansine - chemical synthesis ; Maytansine - chemistry</subject><ispartof>Organic letters, 2006-01, Vol.8 (1), p.135-138</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16381586$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Frenzel, Thomas</creatorcontrib><creatorcontrib>Brünjes, Marco</creatorcontrib><creatorcontrib>Quitschalle, Monika</creatorcontrib><creatorcontrib>Kirschning, Andreas</creatorcontrib><title>Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>[structure: see text] The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.</description><subject>Cysteamine - analogs &amp; derivatives</subject><subject>Cysteamine - chemistry</subject><subject>Esters</subject><subject>Maytansine - analogs &amp; derivatives</subject><subject>Maytansine - chemical synthesis</subject><subject>Maytansine - chemistry</subject><issn>1523-7060</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1jz1PwzAQhj2AaCkM_AHUiS1w_nZGVD6lCgZgjuzkLFwlcRsnQ_49RpTp7t57dO-9hFxRuKXA6F1sQTJpzOGELKlkvNCgYEHOU9oB0KyUZ2RBFTdUGrUkDx9zP35jCmkd_Tp367fC1jjObT2nEW0XesxyiJin4ZdJWMdiP0Tbp7wdYx36C3LqbZvw8lhX5Ovp8XPzUmzfn18399tix7QcC4tKeOO5K0EK5X1jvebYeLDCO1mWzpbWO20UcFEz1kgQQgIyWwqhnWv4itz83c32hyl_VHUh1di2tsc4pUppBTmkyeD1EZxch021H0Jnh7n6z81_ALXpWJA</recordid><startdate>20060105</startdate><enddate>20060105</enddate><creator>Frenzel, Thomas</creator><creator>Brünjes, Marco</creator><creator>Quitschalle, Monika</creator><creator>Kirschning, Andreas</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20060105</creationdate><title>Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin</title><author>Frenzel, Thomas ; Brünjes, Marco ; Quitschalle, Monika ; Kirschning, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j275t-ae64f8f3b90546ffdaf73edf0a4fb599ba9afb786034c22d504450e2a9447bbd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Cysteamine - analogs &amp; derivatives</topic><topic>Cysteamine - chemistry</topic><topic>Esters</topic><topic>Maytansine - analogs &amp; derivatives</topic><topic>Maytansine - chemical synthesis</topic><topic>Maytansine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Frenzel, Thomas</creatorcontrib><creatorcontrib>Brünjes, Marco</creatorcontrib><creatorcontrib>Quitschalle, Monika</creatorcontrib><creatorcontrib>Kirschning, Andreas</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Frenzel, Thomas</au><au>Brünjes, Marco</au><au>Quitschalle, Monika</au><au>Kirschning, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2006-01-05</date><risdate>2006</risdate><volume>8</volume><issue>1</issue><spage>135</spage><epage>138</epage><pages>135-138</pages><issn>1523-7060</issn><abstract>[structure: see text] The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.</abstract><cop>United States</cop><pmid>16381586</pmid><doi>10.1021/ol052588q</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2006-01, Vol.8 (1), p.135-138
issn 1523-7060
language eng
recordid cdi_proquest_miscellaneous_67600018
source MEDLINE; American Chemical Society Journals
subjects Cysteamine - analogs & derivatives
Cysteamine - chemistry
Esters
Maytansine - analogs & derivatives
Maytansine - chemical synthesis
Maytansine - chemistry
title Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T03%3A15%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20the%20N-acetylcysteamine%20thioester%20of%20seco-proansamitocin&rft.jtitle=Organic%20letters&rft.au=Frenzel,%20Thomas&rft.date=2006-01-05&rft.volume=8&rft.issue=1&rft.spage=135&rft.epage=138&rft.pages=135-138&rft.issn=1523-7060&rft_id=info:doi/10.1021/ol052588q&rft_dat=%3Cproquest_pubme%3E67600018%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=67600018&rft_id=info:pmid/16381586&rfr_iscdi=true