Total Synthesis of Murisolins and Evaluation of Tumor-Growth Inhibitory Activity
Convergent total syntheses of murisolin (1), natural 16,19‐cis‐murisolin 2, and unnatural 16,19‐cis‐murisolin 3 were accomplished by asymmetric alkynylation of α‐tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ‐lactone segment as the key steps. Stereoisomers of α‐tetrahydrof...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2005-10, Vol.11 (21), p.6237-6245 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6245 |
|---|---|
| container_issue | 21 |
| container_start_page | 6237 |
| container_title | Chemistry : a European journal |
| container_volume | 11 |
| creator | Maezaki, Naoyoshi Tominaga, Hiroaki Kojima, Naoto Yanai, Minori Urabe, Daisuke Ueki, Risa Tanaka, Tetsuaki Yamori, Takao |
| description | Convergent total syntheses of murisolin (1), natural 16,19‐cis‐murisolin 2, and unnatural 16,19‐cis‐murisolin 3 were accomplished by asymmetric alkynylation of α‐tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ‐lactone segment as the key steps. Stereoisomers of α‐tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6‐heptadiyne proceeded in good yield and with high diastereoselectivity. The cell‐growth inhibition profile and COMPARE analysis of the synthetic compounds 1–3 were also investigated.
Natural versus unnatural: Convergent total syntheses of murisolin, natural 16,19‐cis‐murisolin, and unnatural 16,19‐cis‐murisolin (see structures) were accomplished. The cell‐growth inhibition profile and COMPARE analysis of the compounds were investigated. |
| doi_str_mv | 10.1002/chem.200500462 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68701656</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68701656</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4472-996451f8f5841be6df5c95a716e4fdff856234a59014c84c0f5a97cc12996ff83</originalsourceid><addsrcrecordid>eNqFkM1P2zAYhy00BAV25TjltFvK68Qf8RF1XUGisInCJC6W69qqtyRmtgPkvydVq243Tu_hfZ7n8EPoHMMYAxQXem2acQFAAQgrDtAI0wLnJWf0ExqBIDxntBTH6CTG3wAgWFkeoWPMgFNC8Aj9WPik6uy-b9PaRBczb7N5F1z0tWtjptpVNn1RdaeS8-3muegaH_JZ8K9pnV23a7d0yYc-u9TJvbjUn6FDq-poPu_uKXr4Pl1MrvKbu9n15PIm14TwIheCEYptZWlF8NKwlaVaUMUxM8SurK0oK0qiqABMdEU0WKoE1xoXgzm8y1P0ddt9Dv5vZ2KSjYva1LVqje-iZBUHzCgbwPEW1MHHGIyVz8E1KvQSg9xsKDcbyv2Gg_BlV-6WjVn9w3ejDYDYAq-uNv0HOTm5ms7_j-db18Vk3vauCn8k4yWn8tftTM4K_u3n0yPIRfkO3l-NGw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68701656</pqid></control><display><type>article</type><title>Total Synthesis of Murisolins and Evaluation of Tumor-Growth Inhibitory Activity</title><source>MEDLINE</source><source>Wiley Online Library All Journals</source><creator>Maezaki, Naoyoshi ; Tominaga, Hiroaki ; Kojima, Naoto ; Yanai, Minori ; Urabe, Daisuke ; Ueki, Risa ; Tanaka, Tetsuaki ; Yamori, Takao</creator><creatorcontrib>Maezaki, Naoyoshi ; Tominaga, Hiroaki ; Kojima, Naoto ; Yanai, Minori ; Urabe, Daisuke ; Ueki, Risa ; Tanaka, Tetsuaki ; Yamori, Takao</creatorcontrib><description>Convergent total syntheses of murisolin (1), natural 16,19‐cis‐murisolin 2, and unnatural 16,19‐cis‐murisolin 3 were accomplished by asymmetric alkynylation of α‐tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ‐lactone segment as the key steps. Stereoisomers of α‐tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6‐heptadiyne proceeded in good yield and with high diastereoselectivity. The cell‐growth inhibition profile and COMPARE analysis of the synthetic compounds 1–3 were also investigated.
Natural versus unnatural: Convergent total syntheses of murisolin, natural 16,19‐cis‐murisolin, and unnatural 16,19‐cis‐murisolin (see structures) were accomplished. The cell‐growth inhibition profile and COMPARE analysis of the compounds were investigated.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.200500462</identifier><identifier>PMID: 16075441</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>acetogenins ; Alkynes - chemical synthesis ; Alkynes - pharmacology ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; antitumor agents ; Cell Line, Tumor ; Chromatography, High Pressure Liquid ; Drug Screening Assays, Antitumor ; Furans - chemical synthesis ; Furans - pharmacology ; Humans ; Indicators and Reagents ; Lactones - chemical synthesis ; Lactones - pharmacology ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; murisolin ; natural products ; Spectrophotometry, Infrared ; total synthesis</subject><ispartof>Chemistry : a European journal, 2005-10, Vol.11 (21), p.6237-6245</ispartof><rights>Copyright © 2005 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4472-996451f8f5841be6df5c95a716e4fdff856234a59014c84c0f5a97cc12996ff83</citedby><cites>FETCH-LOGICAL-c4472-996451f8f5841be6df5c95a716e4fdff856234a59014c84c0f5a97cc12996ff83</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%2Fchem.200500462$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27923,27924,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16075441$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maezaki, Naoyoshi</creatorcontrib><creatorcontrib>Tominaga, Hiroaki</creatorcontrib><creatorcontrib>Kojima, Naoto</creatorcontrib><creatorcontrib>Yanai, Minori</creatorcontrib><creatorcontrib>Urabe, Daisuke</creatorcontrib><creatorcontrib>Ueki, Risa</creatorcontrib><creatorcontrib>Tanaka, Tetsuaki</creatorcontrib><creatorcontrib>Yamori, Takao</creatorcontrib><title>Total Synthesis of Murisolins and Evaluation of Tumor-Growth Inhibitory Activity</title><title>Chemistry : a European journal</title><addtitle>Chemistry - A European Journal</addtitle><description>Convergent total syntheses of murisolin (1), natural 16,19‐cis‐murisolin 2, and unnatural 16,19‐cis‐murisolin 3 were accomplished by asymmetric alkynylation of α‐tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ‐lactone segment as the key steps. Stereoisomers of α‐tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6‐heptadiyne proceeded in good yield and with high diastereoselectivity. The cell‐growth inhibition profile and COMPARE analysis of the synthetic compounds 1–3 were also investigated.
Natural versus unnatural: Convergent total syntheses of murisolin, natural 16,19‐cis‐murisolin, and unnatural 16,19‐cis‐murisolin (see structures) were accomplished. The cell‐growth inhibition profile and COMPARE analysis of the compounds were investigated.</description><subject>acetogenins</subject><subject>Alkynes - chemical synthesis</subject><subject>Alkynes - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>antitumor agents</subject><subject>Cell Line, Tumor</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Furans - chemical synthesis</subject><subject>Furans - pharmacology</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>Lactones - chemical synthesis</subject><subject>Lactones - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>murisolin</subject><subject>natural products</subject><subject>Spectrophotometry, Infrared</subject><subject>total synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1P2zAYhy00BAV25TjltFvK68Qf8RF1XUGisInCJC6W69qqtyRmtgPkvydVq243Tu_hfZ7n8EPoHMMYAxQXem2acQFAAQgrDtAI0wLnJWf0ExqBIDxntBTH6CTG3wAgWFkeoWPMgFNC8Aj9WPik6uy-b9PaRBczb7N5F1z0tWtjptpVNn1RdaeS8-3muegaH_JZ8K9pnV23a7d0yYc-u9TJvbjUn6FDq-poPu_uKXr4Pl1MrvKbu9n15PIm14TwIheCEYptZWlF8NKwlaVaUMUxM8SurK0oK0qiqABMdEU0WKoE1xoXgzm8y1P0ddt9Dv5vZ2KSjYva1LVqje-iZBUHzCgbwPEW1MHHGIyVz8E1KvQSg9xsKDcbyv2Gg_BlV-6WjVn9w3ejDYDYAq-uNv0HOTm5ms7_j-db18Vk3vauCn8k4yWn8tftTM4K_u3n0yPIRfkO3l-NGw</recordid><startdate>20051021</startdate><enddate>20051021</enddate><creator>Maezaki, Naoyoshi</creator><creator>Tominaga, Hiroaki</creator><creator>Kojima, Naoto</creator><creator>Yanai, Minori</creator><creator>Urabe, Daisuke</creator><creator>Ueki, Risa</creator><creator>Tanaka, Tetsuaki</creator><creator>Yamori, Takao</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>20051021</creationdate><title>Total Synthesis of Murisolins and Evaluation of Tumor-Growth Inhibitory Activity</title><author>Maezaki, Naoyoshi ; Tominaga, Hiroaki ; Kojima, Naoto ; Yanai, Minori ; Urabe, Daisuke ; Ueki, Risa ; Tanaka, Tetsuaki ; Yamori, Takao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4472-996451f8f5841be6df5c95a716e4fdff856234a59014c84c0f5a97cc12996ff83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>acetogenins</topic><topic>Alkynes - chemical synthesis</topic><topic>Alkynes - pharmacology</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>antitumor agents</topic><topic>Cell Line, Tumor</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Furans - chemical synthesis</topic><topic>Furans - pharmacology</topic><topic>Humans</topic><topic>Indicators and Reagents</topic><topic>Lactones - chemical synthesis</topic><topic>Lactones - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>murisolin</topic><topic>natural products</topic><topic>Spectrophotometry, Infrared</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maezaki, Naoyoshi</creatorcontrib><creatorcontrib>Tominaga, Hiroaki</creatorcontrib><creatorcontrib>Kojima, Naoto</creatorcontrib><creatorcontrib>Yanai, Minori</creatorcontrib><creatorcontrib>Urabe, Daisuke</creatorcontrib><creatorcontrib>Ueki, Risa</creatorcontrib><creatorcontrib>Tanaka, Tetsuaki</creatorcontrib><creatorcontrib>Yamori, Takao</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>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Maezaki, Naoyoshi</au><au>Tominaga, Hiroaki</au><au>Kojima, Naoto</au><au>Yanai, Minori</au><au>Urabe, Daisuke</au><au>Ueki, Risa</au><au>Tanaka, Tetsuaki</au><au>Yamori, Takao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Murisolins and Evaluation of Tumor-Growth Inhibitory Activity</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry - A European Journal</addtitle><date>2005-10-21</date><risdate>2005</risdate><volume>11</volume><issue>21</issue><spage>6237</spage><epage>6245</epage><pages>6237-6245</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Convergent total syntheses of murisolin (1), natural 16,19‐cis‐murisolin 2, and unnatural 16,19‐cis‐murisolin 3 were accomplished by asymmetric alkynylation of α‐tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ‐lactone segment as the key steps. Stereoisomers of α‐tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6‐heptadiyne proceeded in good yield and with high diastereoselectivity. The cell‐growth inhibition profile and COMPARE analysis of the synthetic compounds 1–3 were also investigated.
Natural versus unnatural: Convergent total syntheses of murisolin, natural 16,19‐cis‐murisolin, and unnatural 16,19‐cis‐murisolin (see structures) were accomplished. The cell‐growth inhibition profile and COMPARE analysis of the compounds were investigated.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>16075441</pmid><doi>10.1002/chem.200500462</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2005-10, Vol.11 (21), p.6237-6245 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68701656 |
| source | MEDLINE; Wiley Online Library All Journals |
| subjects | acetogenins Alkynes - chemical synthesis Alkynes - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology antitumor agents Cell Line, Tumor Chromatography, High Pressure Liquid Drug Screening Assays, Antitumor Furans - chemical synthesis Furans - pharmacology Humans Indicators and Reagents Lactones - chemical synthesis Lactones - pharmacology Magnetic Resonance Spectroscopy Mass Spectrometry murisolin natural products Spectrophotometry, Infrared total synthesis |
| title | Total Synthesis of Murisolins and Evaluation of Tumor-Growth Inhibitory Activity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T10%3A15%3A51IST&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=Total%20Synthesis%20of%20Murisolins%20and%20Evaluation%20of%20Tumor-Growth%20Inhibitory%20Activity&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Maezaki,%20Naoyoshi&rft.date=2005-10-21&rft.volume=11&rft.issue=21&rft.spage=6237&rft.epage=6245&rft.pages=6237-6245&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.200500462&rft_dat=%3Cproquest_cross%3E68701656%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=68701656&rft_id=info:pmid/16075441&rfr_iscdi=true |