Time Economical Total Synthesis of (−)-Oseltamivir

Time Economical Total Synthesis of (−)-Oseltamivir

A time economical 60 min total synthesis of (−)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2016-07, Vol.18 (14), p.3426-3429
Hauptverfasser: Hayashi, Yujiro, Ogasawara, Shin
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3429
container_issue 14
container_start_page 3426
container_title Organic letters
container_volume 18
creator Hayashi, Yujiro
Ogasawara, Shin
description A time economical 60 min total synthesis of (−)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of three reagents, namely, diphenylprolinol silyl ether, thiourea, and acid, was developed for a rapid asymmetric Michael reaction with excellent diastereo- and enantioselectivities. All reactions were optimized in terms of not only yield and selectivity but also reaction time.
doi_str_mv 10.1021/acs.orglett.6b01595
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1804861628</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1804861628</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-3dd3bf3400282be26a131f2bad1f933e19355beb499784e8945d25428c6955443</originalsourceid><addsrcrecordid>eNp9kE1OwzAQhS0EoqVwAiSUJSzS-jexl6gqP1KlLihry04ccJXExU6QegPWHJGT4KqhSzYzo9F7bzQfANcIThHEaKaKMHX-rTZdN800REywEzBGDJM0hwyfHucMjsBFCBsIUdyIczDCOck5ycUY0LVtTLIoXOsaW6g6Wbsu1pdd272bYEPiquT25-v7Ll0FU3eqsZ_WX4KzStXBXA19Al4fFuv5U7pcPT7P75epIpR1KSlLoitCIcQca4MzhQiqsFYlqgQhBgnCmDaaCpFzarigrMSMYl5kgjFKyQTcHnK33n30JnSysaEwda1a4_ogEYeUZyjDPErJQVp4F4I3ldx62yi_kwjKPS4ZcckBlxxwRdfNcKDXjSmPnj8-UTA7CPbujet9G__9N_IXrsB36g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1804861628</pqid></control><display><type>article</type><title>Time Economical Total Synthesis of (−)-Oseltamivir</title><source>ACS Publications</source><creator>Hayashi, Yujiro ; Ogasawara, Shin</creator><creatorcontrib>Hayashi, Yujiro ; Ogasawara, Shin</creatorcontrib><description>A time economical 60 min total synthesis of (−)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of three reagents, namely, diphenylprolinol silyl ether, thiourea, and acid, was developed for a rapid asymmetric Michael reaction with excellent diastereo- and enantioselectivities. All reactions were optimized in terms of not only yield and selectivity but also reaction time.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.6b01595</identifier><identifier>PMID: 27378379</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2016-07, Vol.18 (14), p.3426-3429</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-3dd3bf3400282be26a131f2bad1f933e19355beb499784e8945d25428c6955443</citedby><cites>FETCH-LOGICAL-a345t-3dd3bf3400282be26a131f2bad1f933e19355beb499784e8945d25428c6955443</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/acs.orglett.6b01595$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.6b01595$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27378379$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hayashi, Yujiro</creatorcontrib><creatorcontrib>Ogasawara, Shin</creatorcontrib><title>Time Economical Total Synthesis of (−)-Oseltamivir</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A time economical 60 min total synthesis of (−)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of three reagents, namely, diphenylprolinol silyl ether, thiourea, and acid, was developed for a rapid asymmetric Michael reaction with excellent diastereo- and enantioselectivities. All reactions were optimized in terms of not only yield and selectivity but also reaction time.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kE1OwzAQhS0EoqVwAiSUJSzS-jexl6gqP1KlLihry04ccJXExU6QegPWHJGT4KqhSzYzo9F7bzQfANcIThHEaKaKMHX-rTZdN800REywEzBGDJM0hwyfHucMjsBFCBsIUdyIczDCOck5ycUY0LVtTLIoXOsaW6g6Wbsu1pdd272bYEPiquT25-v7Ll0FU3eqsZ_WX4KzStXBXA19Al4fFuv5U7pcPT7P75epIpR1KSlLoitCIcQca4MzhQiqsFYlqgQhBgnCmDaaCpFzarigrMSMYl5kgjFKyQTcHnK33n30JnSysaEwda1a4_ogEYeUZyjDPErJQVp4F4I3ldx62yi_kwjKPS4ZcckBlxxwRdfNcKDXjSmPnj8-UTA7CPbujet9G__9N_IXrsB36g</recordid><startdate>20160715</startdate><enddate>20160715</enddate><creator>Hayashi, Yujiro</creator><creator>Ogasawara, Shin</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20160715</creationdate><title>Time Economical Total Synthesis of (−)-Oseltamivir</title><author>Hayashi, Yujiro ; Ogasawara, Shin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-3dd3bf3400282be26a131f2bad1f933e19355beb499784e8945d25428c6955443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hayashi, Yujiro</creatorcontrib><creatorcontrib>Ogasawara, Shin</creatorcontrib><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>Hayashi, Yujiro</au><au>Ogasawara, Shin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Time Economical Total Synthesis of (−)-Oseltamivir</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2016-07-15</date><risdate>2016</risdate><volume>18</volume><issue>14</issue><spage>3426</spage><epage>3429</epage><pages>3426-3429</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A time economical 60 min total synthesis of (−)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of three reagents, namely, diphenylprolinol silyl ether, thiourea, and acid, was developed for a rapid asymmetric Michael reaction with excellent diastereo- and enantioselectivities. All reactions were optimized in terms of not only yield and selectivity but also reaction time.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>27378379</pmid><doi>10.1021/acs.orglett.6b01595</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2016-07, Vol.18 (14), p.3426-3429
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_1804861628
source ACS Publications
title Time Economical Total Synthesis of (−)-Oseltamivir
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T00%3A37%3A38IST&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=Time%20Economical%20Total%20Synthesis%20of%20(%E2%88%92)-Oseltamivir&rft.jtitle=Organic%20letters&rft.au=Hayashi,%20Yujiro&rft.date=2016-07-15&rft.volume=18&rft.issue=14&rft.spage=3426&rft.epage=3429&rft.pages=3426-3429&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.6b01595&rft_dat=%3Cproquest_cross%3E1804861628%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=1804861628&rft_id=info:pmid/27378379&rfr_iscdi=true