Absolute stereochemistries of the aplysiatoxins and oscillatoxin A

Absolute stereochemistries of the aplysiatoxins and oscillatoxin A

Optical and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallographic analysis of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asymmetric carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-no...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 1984-06, Vol.49 (13), p.2484-2489
Hauptverfasser: Moore, Richard E, Blackman, Adrian J, Cheuk, Chad E, Mynderse, Jon S, Matsumoto, Gayle K, Clardy, Jon, Woodard, Ronald W, Craig, J. Cymerman
Format: Artikel
Sprache:eng
Schlagworte:
Marine
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2489
container_issue 13
container_start_page 2484
container_title Journal of organic chemistry
container_volume 49
creator Moore, Richard E
Blackman, Adrian J
Cheuk, Chad E
Mynderse, Jon S
Matsumoto, Gayle K
Clardy, Jon
Woodard, Ronald W
Craig, J. Cymerman
description Optical and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallographic analysis of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asymmetric carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-nor compound, oscillatoxin A, has the same absolute stereochemistry at C(3), C(4), C(7), C(9), C(10), C(11), C(12), C(15), and C(29).
doi_str_mv 10.1021/jo00187a035
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_14027835</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>14027835</sourcerecordid><originalsourceid>FETCH-LOGICAL-a400t-8e33bcc8526f1f85b4b43447838be7e934f56b081d038b6ca1bbf37cdc3140403</originalsourceid><addsrcrecordid>eNptkE9LAzEUxIMoWKsnv0BOepDVl02yuz3W-heKSlvPIUmzdOt2U_N2of32RlbEg-_yYPgxzAwh5wyuGaTsZu0BWJFr4PKADJhMIclGIA7JACBNE55m_JicIK4hnpRyQG7HBn3dtY5i64LzduU2Fbahckh9SduVo3pb77HSrd9VDVLdLKlHW9V1r9DxKTkqdY3u7OcPyfvD_WLylExfH58n42miBUCbFI5zY20h06xkZSGNMIILkRe8MC53Iy5KmRko2BKiklnNjCl5bpeWMwEC-JBc9L7b4D87h62KSa2LQRrnO1SRSqObjOBVD9rgEYMr1TZUGx32ioH63kn92SnSSU_H2m73i-rwobKc51It3uZqNp3NJ0_iRd1F_rLntcVo1IUmlv7X-QujmXaS</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>14027835</pqid></control><display><type>article</type><title>Absolute stereochemistries of the aplysiatoxins and oscillatoxin A</title><source>ACS Publications</source><creator>Moore, Richard E ; Blackman, Adrian J ; Cheuk, Chad E ; Mynderse, Jon S ; Matsumoto, Gayle K ; Clardy, Jon ; Woodard, Ronald W ; Craig, J. Cymerman</creator><creatorcontrib>Moore, Richard E ; Blackman, Adrian J ; Cheuk, Chad E ; Mynderse, Jon S ; Matsumoto, Gayle K ; Clardy, Jon ; Woodard, Ronald W ; Craig, J. Cymerman</creatorcontrib><description>Optical and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallographic analysis of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asymmetric carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-nor compound, oscillatoxin A, has the same absolute stereochemistry at C(3), C(4), C(7), C(9), C(10), C(11), C(12), C(15), and C(29).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo00187a035</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Marine</subject><ispartof>Journal of organic chemistry, 1984-06, Vol.49 (13), p.2484-2489</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a400t-8e33bcc8526f1f85b4b43447838be7e934f56b081d038b6ca1bbf37cdc3140403</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo00187a035$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo00187a035$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids></links><search><creatorcontrib>Moore, Richard E</creatorcontrib><creatorcontrib>Blackman, Adrian J</creatorcontrib><creatorcontrib>Cheuk, Chad E</creatorcontrib><creatorcontrib>Mynderse, Jon S</creatorcontrib><creatorcontrib>Matsumoto, Gayle K</creatorcontrib><creatorcontrib>Clardy, Jon</creatorcontrib><creatorcontrib>Woodard, Ronald W</creatorcontrib><creatorcontrib>Craig, J. Cymerman</creatorcontrib><title>Absolute stereochemistries of the aplysiatoxins and oscillatoxin A</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Optical and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallographic analysis of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asymmetric carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-nor compound, oscillatoxin A, has the same absolute stereochemistry at C(3), C(4), C(7), C(9), C(10), C(11), C(12), C(15), and C(29).</description><subject>Marine</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><recordid>eNptkE9LAzEUxIMoWKsnv0BOepDVl02yuz3W-heKSlvPIUmzdOt2U_N2of32RlbEg-_yYPgxzAwh5wyuGaTsZu0BWJFr4PKADJhMIclGIA7JACBNE55m_JicIK4hnpRyQG7HBn3dtY5i64LzduU2Fbahckh9SduVo3pb77HSrd9VDVLdLKlHW9V1r9DxKTkqdY3u7OcPyfvD_WLylExfH58n42miBUCbFI5zY20h06xkZSGNMIILkRe8MC53Iy5KmRko2BKiklnNjCl5bpeWMwEC-JBc9L7b4D87h62KSa2LQRrnO1SRSqObjOBVD9rgEYMr1TZUGx32ioH63kn92SnSSU_H2m73i-rwobKc51It3uZqNp3NJ0_iRd1F_rLntcVo1IUmlv7X-QujmXaS</recordid><startdate>198406</startdate><enddate>198406</enddate><creator>Moore, Richard E</creator><creator>Blackman, Adrian J</creator><creator>Cheuk, Chad E</creator><creator>Mynderse, Jon S</creator><creator>Matsumoto, Gayle K</creator><creator>Clardy, Jon</creator><creator>Woodard, Ronald W</creator><creator>Craig, J. Cymerman</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>C1K</scope><scope>F1W</scope><scope>H97</scope><scope>L.G</scope><scope>M7N</scope></search><sort><creationdate>198406</creationdate><title>Absolute stereochemistries of the aplysiatoxins and oscillatoxin A</title><author>Moore, Richard E ; Blackman, Adrian J ; Cheuk, Chad E ; Mynderse, Jon S ; Matsumoto, Gayle K ; Clardy, Jon ; Woodard, Ronald W ; Craig, J. Cymerman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a400t-8e33bcc8526f1f85b4b43447838be7e934f56b081d038b6ca1bbf37cdc3140403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>Marine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moore, Richard E</creatorcontrib><creatorcontrib>Blackman, Adrian J</creatorcontrib><creatorcontrib>Cheuk, Chad E</creatorcontrib><creatorcontrib>Mynderse, Jon S</creatorcontrib><creatorcontrib>Matsumoto, Gayle K</creatorcontrib><creatorcontrib>Clardy, Jon</creatorcontrib><creatorcontrib>Woodard, Ronald W</creatorcontrib><creatorcontrib>Craig, J. Cymerman</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science &amp; Fisheries Abstracts (ASFA) 3: Aquatic Pollution &amp; Environmental Quality</collection><collection>Aquatic Science &amp; Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moore, Richard E</au><au>Blackman, Adrian J</au><au>Cheuk, Chad E</au><au>Mynderse, Jon S</au><au>Matsumoto, Gayle K</au><au>Clardy, Jon</au><au>Woodard, Ronald W</au><au>Craig, J. Cymerman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Absolute stereochemistries of the aplysiatoxins and oscillatoxin A</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1984-06</date><risdate>1984</risdate><volume>49</volume><issue>13</issue><spage>2484</spage><epage>2489</epage><pages>2484-2489</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Optical and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallographic analysis of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asymmetric carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-nor compound, oscillatoxin A, has the same absolute stereochemistry at C(3), C(4), C(7), C(9), C(10), C(11), C(12), C(15), and C(29).</abstract><pub>American Chemical Society</pub><doi>10.1021/jo00187a035</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 1984-06, Vol.49 (13), p.2484-2489
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_14027835
source ACS Publications
subjects Marine
title Absolute stereochemistries of the aplysiatoxins and oscillatoxin A
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T09%3A28%3A09IST&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=Absolute%20stereochemistries%20of%20the%20aplysiatoxins%20and%20oscillatoxin%20A&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Moore,%20Richard%20E&rft.date=1984-06&rft.volume=49&rft.issue=13&rft.spage=2484&rft.epage=2489&rft.pages=2484-2489&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/jo00187a035&rft_dat=%3Cproquest_cross%3E14027835%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=14027835&rft_id=info:pmid/&rfr_iscdi=true