Total Synthesis of (−)-Melotenine A

Total Synthesis of (−)-Melotenine A

'Melo' out: A concise asymmetric synthesis of (−)‐melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N‐tosylindole‐3‐carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one‐pot sequence to pr...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2013-08, Vol.52 (32), p.8309-8311
Hauptverfasser: Zhao, Senzhi, Sirasani, Gopal, Vaddypally, Shivaiah, Zdilla, Michael J., Andrade, Rodrigo B.
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids
annulation
Biological Products - chemical synthesis
Biological Products - chemistry
heterocycles
natural products
Secologanin Tryptamine Alkaloids - chemical synthesis
Secologanin Tryptamine Alkaloids - chemistry
total synthesis
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 8311
container_issue 32
container_start_page 8309
container_title Angewandte Chemie International Edition
container_volume 52
creator Zhao, Senzhi
Sirasani, Gopal
Vaddypally, Shivaiah
Zdilla, Michael J.
Andrade, Rodrigo B.
description 'Melo' out: A concise asymmetric synthesis of (−)‐melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N‐tosylindole‐3‐carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one‐pot sequence to prepare the ABCE tetracycle. Boc=tert‐butoxycarbonyl, Ts=4‐toluenesulfonyl.
doi_str_mv 10.1002/anie.201302517
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1418143292</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1418143292</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3837-4a4d533d98cba7a3547d49ef048f48eb724c94be58959036db03b1c5536ac65f3</originalsourceid><addsrcrecordid>eNqFkEFPwjAYhhujEUWvHg038TBs-7VreyQEEEU0EeOx6bYuTseG64hy82Li2Z_IL3FkSLx56nd43ifpg9AJwR2CMb0wWWI7FBPAlBOxgw4Ip8QDIWC3uhmAJyQnDXTo3HPFS4n9fdSgICSTCh-gs2lemrR1v8zKJ-sS18rjVnv19X3u3dg0L22WZHb18dk9QnuxSZ093rxN9DDoT3uX3vh2OOp1x14IEoTHDIs4QKRkGBhhgDMRMWVjzGTMpA0EZaFigeVScYXBjwIMAQk5B9-EPo-hidq1d17krwvrSj1LXGjT1GQ2XzhNGJHVt6iiFdqp0bDInStsrOdFMjPFUhOs13H0Oo7exqkGpxv3IpjZaIv_1qgAVQNvSWqX_-h0dzLq_5V79TZxpX3fbk3xon0BguvHyVBPBld3YnAt9BB-ANAIfuk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1418143292</pqid></control><display><type>article</type><title>Total Synthesis of (−)-Melotenine A</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Zhao, Senzhi ; Sirasani, Gopal ; Vaddypally, Shivaiah ; Zdilla, Michael J. ; Andrade, Rodrigo B.</creator><creatorcontrib>Zhao, Senzhi ; Sirasani, Gopal ; Vaddypally, Shivaiah ; Zdilla, Michael J. ; Andrade, Rodrigo B.</creatorcontrib><description>'Melo' out: A concise asymmetric synthesis of (−)‐melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N‐tosylindole‐3‐carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one‐pot sequence to prepare the ABCE tetracycle. Boc=tert‐butoxycarbonyl, Ts=4‐toluenesulfonyl.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201302517</identifier><identifier>PMID: 23784890</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkaloids ; annulation ; Biological Products - chemical synthesis ; Biological Products - chemistry ; heterocycles ; natural products ; Secologanin Tryptamine Alkaloids - chemical synthesis ; Secologanin Tryptamine Alkaloids - chemistry ; total synthesis</subject><ispartof>Angewandte Chemie International Edition, 2013-08, Vol.52 (32), p.8309-8311</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3837-4a4d533d98cba7a3547d49ef048f48eb724c94be58959036db03b1c5536ac65f3</citedby><cites>FETCH-LOGICAL-c3837-4a4d533d98cba7a3547d49ef048f48eb724c94be58959036db03b1c5536ac65f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201302517$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201302517$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27911,27912,45561,45562</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23784890$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhao, Senzhi</creatorcontrib><creatorcontrib>Sirasani, Gopal</creatorcontrib><creatorcontrib>Vaddypally, Shivaiah</creatorcontrib><creatorcontrib>Zdilla, Michael J.</creatorcontrib><creatorcontrib>Andrade, Rodrigo B.</creatorcontrib><title>Total Synthesis of (−)-Melotenine A</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>'Melo' out: A concise asymmetric synthesis of (−)‐melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N‐tosylindole‐3‐carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one‐pot sequence to prepare the ABCE tetracycle. Boc=tert‐butoxycarbonyl, Ts=4‐toluenesulfonyl.</description><subject>Alkaloids</subject><subject>annulation</subject><subject>Biological Products - chemical synthesis</subject><subject>Biological Products - chemistry</subject><subject>heterocycles</subject><subject>natural products</subject><subject>Secologanin Tryptamine Alkaloids - chemical synthesis</subject><subject>Secologanin Tryptamine Alkaloids - chemistry</subject><subject>total synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEFPwjAYhhujEUWvHg038TBs-7VreyQEEEU0EeOx6bYuTseG64hy82Li2Z_IL3FkSLx56nd43ifpg9AJwR2CMb0wWWI7FBPAlBOxgw4Ip8QDIWC3uhmAJyQnDXTo3HPFS4n9fdSgICSTCh-gs2lemrR1v8zKJ-sS18rjVnv19X3u3dg0L22WZHb18dk9QnuxSZ093rxN9DDoT3uX3vh2OOp1x14IEoTHDIs4QKRkGBhhgDMRMWVjzGTMpA0EZaFigeVScYXBjwIMAQk5B9-EPo-hidq1d17krwvrSj1LXGjT1GQ2XzhNGJHVt6iiFdqp0bDInStsrOdFMjPFUhOs13H0Oo7exqkGpxv3IpjZaIv_1qgAVQNvSWqX_-h0dzLq_5V79TZxpX3fbk3xon0BguvHyVBPBld3YnAt9BB-ANAIfuk</recordid><startdate>20130805</startdate><enddate>20130805</enddate><creator>Zhao, Senzhi</creator><creator>Sirasani, Gopal</creator><creator>Vaddypally, Shivaiah</creator><creator>Zdilla, Michael J.</creator><creator>Andrade, Rodrigo B.</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>20130805</creationdate><title>Total Synthesis of (−)-Melotenine A</title><author>Zhao, Senzhi ; Sirasani, Gopal ; Vaddypally, Shivaiah ; Zdilla, Michael J. ; Andrade, Rodrigo B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3837-4a4d533d98cba7a3547d49ef048f48eb724c94be58959036db03b1c5536ac65f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkaloids</topic><topic>annulation</topic><topic>Biological Products - chemical synthesis</topic><topic>Biological Products - chemistry</topic><topic>heterocycles</topic><topic>natural products</topic><topic>Secologanin Tryptamine Alkaloids - chemical synthesis</topic><topic>Secologanin Tryptamine Alkaloids - chemistry</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhao, Senzhi</creatorcontrib><creatorcontrib>Sirasani, Gopal</creatorcontrib><creatorcontrib>Vaddypally, Shivaiah</creatorcontrib><creatorcontrib>Zdilla, Michael J.</creatorcontrib><creatorcontrib>Andrade, Rodrigo B.</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>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhao, Senzhi</au><au>Sirasani, Gopal</au><au>Vaddypally, Shivaiah</au><au>Zdilla, Michael J.</au><au>Andrade, Rodrigo B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of (−)-Melotenine A</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2013-08-05</date><risdate>2013</risdate><volume>52</volume><issue>32</issue><spage>8309</spage><epage>8311</epage><pages>8309-8311</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>'Melo' out: A concise asymmetric synthesis of (−)‐melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N‐tosylindole‐3‐carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one‐pot sequence to prepare the ABCE tetracycle. Boc=tert‐butoxycarbonyl, Ts=4‐toluenesulfonyl.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>23784890</pmid><doi>10.1002/anie.201302517</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie International Edition, 2013-08, Vol.52 (32), p.8309-8311
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_1418143292
source MEDLINE; Wiley Online Library Journals Frontfile Complete
subjects Alkaloids
annulation
Biological Products - chemical synthesis
Biological Products - chemistry
heterocycles
natural products
Secologanin Tryptamine Alkaloids - chemical synthesis
Secologanin Tryptamine Alkaloids - chemistry
total synthesis
title Total Synthesis of (−)-Melotenine A
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T16%3A25%3A20IST&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%20(%E2%88%92)-Melotenine%E2%80%85A&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Zhao,%20Senzhi&rft.date=2013-08-05&rft.volume=52&rft.issue=32&rft.spage=8309&rft.epage=8311&rft.pages=8309-8311&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201302517&rft_dat=%3Cproquest_cross%3E1418143292%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=1418143292&rft_id=info:pmid/23784890&rfr_iscdi=true