A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine

A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine

A simple synthesis of the title compounds, which is more than 10 steps shorter and an order of magnitude more efficient than our recent photochemical synthesis of chasmanine, is described. The main feature of the new process is a stereo- and regiospecific addition of benzyl vinyl ether to an o-quino...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Canadian journal of chemistry 1978-05, Vol.56 (10), p.1451-1454
Hauptverfasser: Wiesner, Karel, Tsai, Thomas Y. R, Nambiar, Krishnan P
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1454
container_issue 10
container_start_page 1451
container_title Canadian journal of chemistry
container_volume 56
creator Wiesner, Karel
Tsai, Thomas Y. R
Nambiar, Krishnan P
description A simple synthesis of the title compounds, which is more than 10 steps shorter and an order of magnitude more efficient than our recent photochemical synthesis of chasmanine, is described. The main feature of the new process is a stereo- and regiospecific addition of benzyl vinyl ether to an o-quinone intermediate masked by a spirolactone group according to the method of Deslongchamps.
doi_str_mv 10.1139/v78-237
format Article
fullrecord <record><control><sourceid>crossref_nrcre</sourceid><recordid>TN_cdi_crossref_primary_10_1139_v78_237</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1139_v78_237</sourcerecordid><originalsourceid>FETCH-LOGICAL-c287t-ab27e651632ebcf521fd5cc62be983c95eaf11f1a438d6d6f7def0d36c6b45e03</originalsourceid><addsrcrecordid>eNp10EtLxDAUBeAgCo6j-BeyUhCiebRJuxwGnwy40XVJkxta6TQlt6j993aYwYXg6nIuH2dxCLkU_FYIVd59moJJZY7IQmQFZ0qW4pgsOOcFy3gmT8kZ4sccDZf5grysaA9fFEdIEHEA14bW0TGOtqM49WMD2CKNgbrG4tb2bQ_U9p4KxTxg_J48dEMTd_9zchJsh3BxuEvy_nD_tn5im9fH5_Vqw5wszMhsLQ3oXGgloXYhlyL43DktaygL5cocbBAiCJupwmuvg_EQuFfa6TrLgaslud73uhQRE4RqSO3WpqkSvNpNUM0TVPMEs7zayz65BAg2ueYXH1A1-DDDm__h39YfnkJrWg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine</title><source>NRC Research Press</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Wiesner, Karel ; Tsai, Thomas Y. R ; Nambiar, Krishnan P</creator><creatorcontrib>Wiesner, Karel ; Tsai, Thomas Y. R ; Nambiar, Krishnan P</creatorcontrib><description>A simple synthesis of the title compounds, which is more than 10 steps shorter and an order of magnitude more efficient than our recent photochemical synthesis of chasmanine, is described. The main feature of the new process is a stereo- and regiospecific addition of benzyl vinyl ether to an o-quinone intermediate masked by a spirolactone group according to the method of Deslongchamps.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v78-237</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 1978-05, Vol.56 (10), p.1451-1454</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c287t-ab27e651632ebcf521fd5cc62be983c95eaf11f1a438d6d6f7def0d36c6b45e03</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v78-237$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v78-237$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,780,784,2932,27924,27925,64428,65234</link.rule.ids></links><search><creatorcontrib>Wiesner, Karel</creatorcontrib><creatorcontrib>Tsai, Thomas Y. R</creatorcontrib><creatorcontrib>Nambiar, Krishnan P</creatorcontrib><title>A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>A simple synthesis of the title compounds, which is more than 10 steps shorter and an order of magnitude more efficient than our recent photochemical synthesis of chasmanine, is described. The main feature of the new process is a stereo- and regiospecific addition of benzyl vinyl ether to an o-quinone intermediate masked by a spirolactone group according to the method of Deslongchamps.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1978</creationdate><recordtype>article</recordtype><recordid>eNp10EtLxDAUBeAgCo6j-BeyUhCiebRJuxwGnwy40XVJkxta6TQlt6j993aYwYXg6nIuH2dxCLkU_FYIVd59moJJZY7IQmQFZ0qW4pgsOOcFy3gmT8kZ4sccDZf5grysaA9fFEdIEHEA14bW0TGOtqM49WMD2CKNgbrG4tb2bQ_U9p4KxTxg_J48dEMTd_9zchJsh3BxuEvy_nD_tn5im9fH5_Vqw5wszMhsLQ3oXGgloXYhlyL43DktaygL5cocbBAiCJupwmuvg_EQuFfa6TrLgaslud73uhQRE4RqSO3WpqkSvNpNUM0TVPMEs7zayz65BAg2ueYXH1A1-DDDm__h39YfnkJrWg</recordid><startdate>19780515</startdate><enddate>19780515</enddate><creator>Wiesner, Karel</creator><creator>Tsai, Thomas Y. R</creator><creator>Nambiar, Krishnan P</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19780515</creationdate><title>A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine</title><author>Wiesner, Karel ; Tsai, Thomas Y. R ; Nambiar, Krishnan P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c287t-ab27e651632ebcf521fd5cc62be983c95eaf11f1a438d6d6f7def0d36c6b45e03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wiesner, Karel</creatorcontrib><creatorcontrib>Tsai, Thomas Y. R</creatorcontrib><creatorcontrib>Nambiar, Krishnan P</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wiesner, Karel</au><au>Tsai, Thomas Y. R</au><au>Nambiar, Krishnan P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1978-05-15</date><risdate>1978</risdate><volume>56</volume><issue>10</issue><spage>1451</spage><epage>1454</epage><pages>1451-1454</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>A simple synthesis of the title compounds, which is more than 10 steps shorter and an order of magnitude more efficient than our recent photochemical synthesis of chasmanine, is described. The main feature of the new process is a stereo- and regiospecific addition of benzyl vinyl ether to an o-quinone intermediate masked by a spirolactone group according to the method of Deslongchamps.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v78-237</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0008-4042
ispartof Canadian journal of chemistry, 1978-05, Vol.56 (10), p.1451-1454
issn 0008-4042
1480-3291
language eng
recordid cdi_crossref_primary_10_1139_v78_237
source NRC Research Press; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry
title A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-22T18%3A39%3A31IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref_nrcre&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20new%20stereospecific%20total%20synthesis%20of%20chasmanine%20and%2013-desoxydelphonine&rft.jtitle=Canadian%20journal%20of%20chemistry&rft.au=Wiesner,%20Karel&rft.date=1978-05-15&rft.volume=56&rft.issue=10&rft.spage=1451&rft.epage=1454&rft.pages=1451-1454&rft.issn=0008-4042&rft.eissn=1480-3291&rft_id=info:doi/10.1139/v78-237&rft_dat=%3Ccrossref_nrcre%3E10_1139_v78_237%3C/crossref_nrcre%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true