Concise, Stereoselective Syntheses of cis-Nemorensic Acid and 4-Hydroxy-cis-nemorensic Acid via Tandem Carbonyl Ylide Formation−Cycloaddition

1,3-Dipolar cycloaddition of propargyl bromide with the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in concise syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid.

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2002-05, Vol.4 (10), p.1809-1811
Hauptverfasser: Hodgson, David M, Avery, Thomas D, Donohue, Andrew C
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1811
container_issue 10
container_start_page 1809
container_title Organic letters
container_volume 4
creator Hodgson, David M
Avery, Thomas D
Donohue, Andrew C
description 1,3-Dipolar cycloaddition of propargyl bromide with the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in concise syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid.
doi_str_mv 10.1021/ol025917c
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71673395</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71673395</sourcerecordid><originalsourceid>FETCH-LOGICAL-a377t-c65c34f1ec8ce53dfa826c77cb1a813fa91c6fed8271d3d8db8f4c6b7e3f29793</originalsourceid><addsrcrecordid>eNpt0MtKxTAQBuAgiveFLyDZKAhWk-a0aZdSvIHoQl24KulkgpE20aRH7Bu4E3xEn8QezkFBXGUyfPwwPyE7nB1xlvJj37I0K7mEJbLOs1QkkmXp8s-cszWyEeMTY3zclKtkjaeMMcGydfJReQc24iG97TGgj9gi9PYV6e3g-keMGKk3dCTJNXY-oIsW6AlYTZXTdJJcDDr4tyGZCfdHvFpF70aGHa1UaLwbWvrQWo30zIdO9da7r_fPaoDWK63t7L9FVoxqI24v3k1yf3Z6V10kVzfnl9XJVaKElH0CeQZiYjhCAZgJbVSR5iAlNFwVXBhVcsgN6iKVXAtd6KYwE8gbicKkpSzFJtmf5z4H_zLF2NedjYBtqxz6aawlz6UQZTbCgzmE4GMMaOrnYDsVhpqzetZ-_dP-aHcXodOmQ_0rF3WPYG8OFMT6yU-DG2_8J-gbhSiPgA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71673395</pqid></control><display><type>article</type><title>Concise, Stereoselective Syntheses of cis-Nemorensic Acid and 4-Hydroxy-cis-nemorensic Acid via Tandem Carbonyl Ylide Formation−Cycloaddition</title><source>MEDLINE</source><source>ACS Publications</source><creator>Hodgson, David M ; Avery, Thomas D ; Donohue, Andrew C</creator><creatorcontrib>Hodgson, David M ; Avery, Thomas D ; Donohue, Andrew C</creatorcontrib><description>1,3-Dipolar cycloaddition of propargyl bromide with the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in concise syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol025917c</identifier><identifier>PMID: 12000305</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antineoplastic Agents, Phytogenic - chemical synthesis ; Catalysis ; Crystallography, X-Ray ; Cyclization ; Furans - chemical synthesis ; Furans - pharmacology ; Models, Molecular ; Pargyline - analogs &amp; derivatives ; Pargyline - chemical synthesis ; Pargyline - pharmacology ; Pyrrolizidine Alkaloids - chemical synthesis ; Pyrrolizidine Alkaloids - pharmacology ; Senecio - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2002-05, Vol.4 (10), p.1809-1811</ispartof><rights>Copyright © 2002 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-c65c34f1ec8ce53dfa826c77cb1a813fa91c6fed8271d3d8db8f4c6b7e3f29793</citedby><cites>FETCH-LOGICAL-a377t-c65c34f1ec8ce53dfa826c77cb1a813fa91c6fed8271d3d8db8f4c6b7e3f29793</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol025917c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol025917c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12000305$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hodgson, David M</creatorcontrib><creatorcontrib>Avery, Thomas D</creatorcontrib><creatorcontrib>Donohue, Andrew C</creatorcontrib><title>Concise, Stereoselective Syntheses of cis-Nemorensic Acid and 4-Hydroxy-cis-nemorensic Acid via Tandem Carbonyl Ylide Formation−Cycloaddition</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>1,3-Dipolar cycloaddition of propargyl bromide with the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in concise syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid.</description><subject>Antineoplastic Agents, Phytogenic - chemical synthesis</subject><subject>Catalysis</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>Furans - chemical synthesis</subject><subject>Furans - pharmacology</subject><subject>Models, Molecular</subject><subject>Pargyline - analogs &amp; derivatives</subject><subject>Pargyline - chemical synthesis</subject><subject>Pargyline - pharmacology</subject><subject>Pyrrolizidine Alkaloids - chemical synthesis</subject><subject>Pyrrolizidine Alkaloids - pharmacology</subject><subject>Senecio - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtKxTAQBuAgiveFLyDZKAhWk-a0aZdSvIHoQl24KulkgpE20aRH7Bu4E3xEn8QezkFBXGUyfPwwPyE7nB1xlvJj37I0K7mEJbLOs1QkkmXp8s-cszWyEeMTY3zclKtkjaeMMcGydfJReQc24iG97TGgj9gi9PYV6e3g-keMGKk3dCTJNXY-oIsW6AlYTZXTdJJcDDr4tyGZCfdHvFpF70aGHa1UaLwbWvrQWo30zIdO9da7r_fPaoDWK63t7L9FVoxqI24v3k1yf3Z6V10kVzfnl9XJVaKElH0CeQZiYjhCAZgJbVSR5iAlNFwVXBhVcsgN6iKVXAtd6KYwE8gbicKkpSzFJtmf5z4H_zLF2NedjYBtqxz6aawlz6UQZTbCgzmE4GMMaOrnYDsVhpqzetZ-_dP-aHcXodOmQ_0rF3WPYG8OFMT6yU-DG2_8J-gbhSiPgA</recordid><startdate>20020516</startdate><enddate>20020516</enddate><creator>Hodgson, David M</creator><creator>Avery, Thomas D</creator><creator>Donohue, Andrew C</creator><general>American Chemical Society</general><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>20020516</creationdate><title>Concise, Stereoselective Syntheses of cis-Nemorensic Acid and 4-Hydroxy-cis-nemorensic Acid via Tandem Carbonyl Ylide Formation−Cycloaddition</title><author>Hodgson, David M ; Avery, Thomas D ; Donohue, Andrew C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-c65c34f1ec8ce53dfa826c77cb1a813fa91c6fed8271d3d8db8f4c6b7e3f29793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Antineoplastic Agents, Phytogenic - chemical synthesis</topic><topic>Catalysis</topic><topic>Crystallography, X-Ray</topic><topic>Cyclization</topic><topic>Furans - chemical synthesis</topic><topic>Furans - pharmacology</topic><topic>Models, Molecular</topic><topic>Pargyline - analogs &amp; derivatives</topic><topic>Pargyline - chemical synthesis</topic><topic>Pargyline - pharmacology</topic><topic>Pyrrolizidine Alkaloids - chemical synthesis</topic><topic>Pyrrolizidine Alkaloids - pharmacology</topic><topic>Senecio - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hodgson, David M</creatorcontrib><creatorcontrib>Avery, Thomas D</creatorcontrib><creatorcontrib>Donohue, Andrew C</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hodgson, David M</au><au>Avery, Thomas D</au><au>Donohue, Andrew C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Concise, Stereoselective Syntheses of cis-Nemorensic Acid and 4-Hydroxy-cis-nemorensic Acid via Tandem Carbonyl Ylide Formation−Cycloaddition</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2002-05-16</date><risdate>2002</risdate><volume>4</volume><issue>10</issue><spage>1809</spage><epage>1811</epage><pages>1809-1811</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>1,3-Dipolar cycloaddition of propargyl bromide with the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in concise syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12000305</pmid><doi>10.1021/ol025917c</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2002-05, Vol.4 (10), p.1809-1811
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_71673395
source MEDLINE; ACS Publications
subjects Antineoplastic Agents, Phytogenic - chemical synthesis
Catalysis
Crystallography, X-Ray
Cyclization
Furans - chemical synthesis
Furans - pharmacology
Models, Molecular
Pargyline - analogs & derivatives
Pargyline - chemical synthesis
Pargyline - pharmacology
Pyrrolizidine Alkaloids - chemical synthesis
Pyrrolizidine Alkaloids - pharmacology
Senecio - chemistry
Stereoisomerism
title Concise, Stereoselective Syntheses of cis-Nemorensic Acid and 4-Hydroxy-cis-nemorensic Acid via Tandem Carbonyl Ylide Formation−Cycloaddition
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-12T13%3A10%3A02IST&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=Concise,%20Stereoselective%20Syntheses%20of%20cis-Nemorensic%20Acid%20and%204-Hydroxy-cis-nemorensic%20Acid%20via%20Tandem%20Carbonyl%20Ylide%20Formation%E2%88%92Cycloaddition&rft.jtitle=Organic%20letters&rft.au=Hodgson,%20David%20M&rft.date=2002-05-16&rft.volume=4&rft.issue=10&rft.spage=1809&rft.epage=1811&rft.pages=1809-1811&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol025917c&rft_dat=%3Cproquest_cross%3E71673395%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=71673395&rft_id=info:pmid/12000305&rfr_iscdi=true