The First Stereoselective Total Synthesis of a Naturally Occurring Bioactive Diarylheptanoid, (3R,6E)-1,7-Bis(4-hydroxyphenyl)hept-6-en-3-ol, through Two Different Approaches

The stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)‐1,7‐bis(4‐hydroxyphenyl)hept‐6‐en‐3‐ol, has been accomplished starting from 4‐hydroxybenzaldehyde through two different approaches involving Wittig olefination, hydrolytic kinetic resolution of a racemic...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Helvetica chimica acta 2012-09, Vol.95 (9), p.1666-1671
Hauptverfasser:	Kashanna, Jajula, Jangili, Paramesh, Kumar, Rathod Aravind, Das, Biswanath
Format:	Artikel
Sprache:	eng
Schlagworte:	diaryl Heptanoid Heptanoid, diaryl Kinetic resolution Stereoselective synthesis Total synthesis Wittig olefination
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	1671
container_issue	9
container_start_page	1666
container_title	Helvetica chimica acta
container_volume	95
creator	Kashanna, Jajula Jangili, Paramesh Kumar, Rathod Aravind Das, Biswanath
description	The stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)‐1,7‐bis(4‐hydroxyphenyl)hept‐6‐en‐3‐ol, has been accomplished starting from 4‐hydroxybenzaldehyde through two different approaches involving Wittig olefination, hydrolytic kinetic resolution of a racemic epoxide, and olefin cross‐metathesis reaction as the key steps.
doi_str_mv	10.1002/hlca.201200084
format	Article
fullrecord	<record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_hlca_201200084</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>HLCA201200084</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3274-d75ea66c1d4969b71b4801eb4654934b7278e6001ad7fc08f2dbc01c08db4c353</originalsourceid><addsrcrecordid>eNqFkM1u2zAQhImiAeomvfbMYwKYDklJpHS0nR8nMBygUdHeCIqiIrasKJB0E71Un7E0HAS99bR7mG92dgD4TPCCYEwve6vkgmJCMcZl_g7MSEEpoowX78EMY1IiTKrvH8DHEH4kSVVhPgN_6l7DG-NDhI9Re-2CtlpF81vD2kVp4eM0xF4HE6DroIQ7GfdeWjvBB6X23pvhCa6Mk0fkykg_2V6PUQ7OtHN4nn2Zs-sLROYcrUw4z1E_td69TGOvh8leHKSIIT2gDDk7h7H3bv_Uw_rZJbOuS4mGCJfj6NOJFOMMnHTSBv3pdZ6CrzfX9XqDtg-3d-vlFqmM8hy1vNCSMUXavGJVw0mTl5joJmdFXmV5wykvNUudyJZ3CpcdbRuFSdraJldZkZ2CxdFXeReC150YvfmVnhMEi0Pb4tC2eGs7AdUReDZWT_9Ri812vfyXRUfWhKhf3ljpfwrGM16Ib7tbQVer3QbXV-I--wvYV5Qo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>The First Stereoselective Total Synthesis of a Naturally Occurring Bioactive Diarylheptanoid, (3R,6E)-1,7-Bis(4-hydroxyphenyl)hept-6-en-3-ol, through Two Different Approaches</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Kashanna, Jajula ; Jangili, Paramesh ; Kumar, Rathod Aravind ; Das, Biswanath</creator><creatorcontrib>Kashanna, Jajula ; Jangili, Paramesh ; Kumar, Rathod Aravind ; Das, Biswanath</creatorcontrib><description>The stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)‐1,7‐bis(4‐hydroxyphenyl)hept‐6‐en‐3‐ol, has been accomplished starting from 4‐hydroxybenzaldehyde through two different approaches involving Wittig olefination, hydrolytic kinetic resolution of a racemic epoxide, and olefin cross‐metathesis reaction as the key steps.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.201200084</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>diaryl ; Heptanoid ; Heptanoid, diaryl ; Kinetic resolution ; Stereoselective synthesis ; Total synthesis ; Wittig olefination</subject><ispartof>Helvetica chimica acta, 2012-09, Vol.95 (9), p.1666-1671</ispartof><rights>Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3274-d75ea66c1d4969b71b4801eb4654934b7278e6001ad7fc08f2dbc01c08db4c353</citedby><cites>FETCH-LOGICAL-c3274-d75ea66c1d4969b71b4801eb4654934b7278e6001ad7fc08f2dbc01c08db4c353</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%2Fhlca.201200084$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.201200084$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Kashanna, Jajula</creatorcontrib><creatorcontrib>Jangili, Paramesh</creatorcontrib><creatorcontrib>Kumar, Rathod Aravind</creatorcontrib><creatorcontrib>Das, Biswanath</creatorcontrib><title>The First Stereoselective Total Synthesis of a Naturally Occurring Bioactive Diarylheptanoid, (3R,6E)-1,7-Bis(4-hydroxyphenyl)hept-6-en-3-ol, through Two Different Approaches</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>The stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)‐1,7‐bis(4‐hydroxyphenyl)hept‐6‐en‐3‐ol, has been accomplished starting from 4‐hydroxybenzaldehyde through two different approaches involving Wittig olefination, hydrolytic kinetic resolution of a racemic epoxide, and olefin cross‐metathesis reaction as the key steps.</description><subject>diaryl</subject><subject>Heptanoid</subject><subject>Heptanoid, diaryl</subject><subject>Kinetic resolution</subject><subject>Stereoselective synthesis</subject><subject>Total synthesis</subject><subject>Wittig olefination</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkM1u2zAQhImiAeomvfbMYwKYDklJpHS0nR8nMBygUdHeCIqiIrasKJB0E71Un7E0HAS99bR7mG92dgD4TPCCYEwve6vkgmJCMcZl_g7MSEEpoowX78EMY1IiTKrvH8DHEH4kSVVhPgN_6l7DG-NDhI9Re-2CtlpF81vD2kVp4eM0xF4HE6DroIQ7GfdeWjvBB6X23pvhCa6Mk0fkykg_2V6PUQ7OtHN4nn2Zs-sLROYcrUw4z1E_td69TGOvh8leHKSIIT2gDDk7h7H3bv_Uw_rZJbOuS4mGCJfj6NOJFOMMnHTSBv3pdZ6CrzfX9XqDtg-3d-vlFqmM8hy1vNCSMUXavGJVw0mTl5joJmdFXmV5wykvNUudyJZ3CpcdbRuFSdraJldZkZ2CxdFXeReC150YvfmVnhMEi0Pb4tC2eGs7AdUReDZWT_9Ri812vfyXRUfWhKhf3ljpfwrGM16Ib7tbQVer3QbXV-I--wvYV5Qo</recordid><startdate>201209</startdate><enddate>201209</enddate><creator>Kashanna, Jajula</creator><creator>Jangili, Paramesh</creator><creator>Kumar, Rathod Aravind</creator><creator>Das, Biswanath</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201209</creationdate><title>The First Stereoselective Total Synthesis of a Naturally Occurring Bioactive Diarylheptanoid, (3R,6E)-1,7-Bis(4-hydroxyphenyl)hept-6-en-3-ol, through Two Different Approaches</title><author>Kashanna, Jajula ; Jangili, Paramesh ; Kumar, Rathod Aravind ; Das, Biswanath</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3274-d75ea66c1d4969b71b4801eb4654934b7278e6001ad7fc08f2dbc01c08db4c353</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>diaryl</topic><topic>Heptanoid</topic><topic>Heptanoid, diaryl</topic><topic>Kinetic resolution</topic><topic>Stereoselective synthesis</topic><topic>Total synthesis</topic><topic>Wittig olefination</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kashanna, Jajula</creatorcontrib><creatorcontrib>Jangili, Paramesh</creatorcontrib><creatorcontrib>Kumar, Rathod Aravind</creatorcontrib><creatorcontrib>Das, Biswanath</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kashanna, Jajula</au><au>Jangili, Paramesh</au><au>Kumar, Rathod Aravind</au><au>Das, Biswanath</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The First Stereoselective Total Synthesis of a Naturally Occurring Bioactive Diarylheptanoid, (3R,6E)-1,7-Bis(4-hydroxyphenyl)hept-6-en-3-ol, through Two Different Approaches</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>2012-09</date><risdate>2012</risdate><volume>95</volume><issue>9</issue><spage>1666</spage><epage>1671</epage><pages>1666-1671</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>The stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)‐1,7‐bis(4‐hydroxyphenyl)hept‐6‐en‐3‐ol, has been accomplished starting from 4‐hydroxybenzaldehyde through two different approaches involving Wittig olefination, hydrolytic kinetic resolution of a racemic epoxide, and olefin cross‐metathesis reaction as the key steps.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/hlca.201200084</doi><tpages>6</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0018-019X
ispartof	Helvetica chimica acta, 2012-09, Vol.95 (9), p.1666-1671
issn	0018-019X 1522-2675
language	eng
recordid	cdi_crossref_primary_10_1002_hlca_201200084
source	Wiley Online Library Journals Frontfile Complete
subjects	diaryl Heptanoid Heptanoid, diaryl Kinetic resolution Stereoselective synthesis Total synthesis Wittig olefination
title	The First Stereoselective Total Synthesis of a Naturally Occurring Bioactive Diarylheptanoid, (3R,6E)-1,7-Bis(4-hydroxyphenyl)hept-6-en-3-ol, through Two Different Approaches
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T13%3A20%3A09IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20First%20Stereoselective%20Total%20Synthesis%20of%20a%20Naturally%20Occurring%20Bioactive%20Diarylheptanoid,%20(3R,6E)-1,7-Bis(4-hydroxyphenyl)hept-6-en-3-ol,%20through%20Two%20Different%20Approaches&rft.jtitle=Helvetica%20chimica%20acta&rft.au=Kashanna,%20Jajula&rft.date=2012-09&rft.volume=95&rft.issue=9&rft.spage=1666&rft.epage=1671&rft.pages=1666-1671&rft.issn=0018-019X&rft.eissn=1522-2675&rft_id=info:doi/10.1002/hlca.201200084&rft_dat=%3Cwiley_cross%3EHLCA201200084%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true