Harnessing Quinone Methides: Total Synthesis of (±)-VaticanolA

Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vatican...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Angewandte Chemie International Edition 2014-06, Vol.53 (26), p.6747-6751
Hauptverfasser:	Jepsen, Tue H, Thomas, Stephen B, Lin, Yunqing, Stathakis, Christos I, deMiguel, Irene, Snyder, Scott A
Format:	Artikel
Sprache:	eng
Schlagworte:	Bonding Congeners Forges Formations Quinones Series (mathematics) Strategy Synthesis Trimers
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	6751
container_issue	26
container_start_page	6747
container_title	Angewandte Chemie International Edition
container_volume	53
creator	Jepsen, Tue H Thomas, Stephen B Lin, Yunqing Stathakis, Christos I deMiguel, Irene Snyder, Scott A
description	Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.
doi_str_mv	10.1002/anie.201402858
format	Article
fullrecord	<record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_1701101955</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1701101955</sourcerecordid><originalsourceid>FETCH-LOGICAL-p131t-c8ad64a1a578ad432b9cec66a61dad4f574ca83627764203bea93295042487983</originalsourceid><addsrcrecordid>eNpdjs1Kw0AUhQdRsFa3rgNu6iJ17tz5ixspRa1QEbG6DbfJ1E6JM7WTLPpYvoJPZkBXrs534ONwGDsHPgbOxRUF78aCg-TCKnvABqAE5GgMHvYsEXNjFRyzk5Q2vW8t1wN2M6NdcCn58J49dz7E4LJH16597dJ1togtNdnLPrRrl3zK4iobfX9d5m_U-opCbCan7GhFTXJnfzlkr3e3i-ksnz_dP0wn83wLCG1eWaq1JCBlepIolkXlKq1JQ933lTKyIotaGKOl4Lh0VKAoFJdCWlNYHLLR7-52Fz87l9ryw6fKNQ0FF7tUguEAHAqlevXin7qJ3S7070pQaDRagxJ_AHztWBs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1537638734</pqid></control><display><type>article</type><title>Harnessing Quinone Methides: Total Synthesis of (±)-VaticanolA</title><source>Access via Wiley Online Library</source><creator>Jepsen, Tue H ; Thomas, Stephen B ; Lin, Yunqing ; Stathakis, Christos I ; deMiguel, Irene ; Snyder, Scott A</creator><creatorcontrib>Jepsen, Tue H ; Thomas, Stephen B ; Lin, Yunqing ; Stathakis, Christos I ; deMiguel, Irene ; Snyder, Scott A</creatorcontrib><description>Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201402858</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Bonding ; Congeners ; Forges ; Formations ; Quinones ; Series (mathematics) ; Strategy ; Synthesis ; Trimers</subject><ispartof>Angewandte Chemie International Edition, 2014-06, Vol.53 (26), p.6747-6751</ispartof><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930</link.rule.ids></links><search><creatorcontrib>Jepsen, Tue H</creatorcontrib><creatorcontrib>Thomas, Stephen B</creatorcontrib><creatorcontrib>Lin, Yunqing</creatorcontrib><creatorcontrib>Stathakis, Christos I</creatorcontrib><creatorcontrib>deMiguel, Irene</creatorcontrib><creatorcontrib>Snyder, Scott A</creatorcontrib><title>Harnessing Quinone Methides: Total Synthesis of (±)-VaticanolA</title><title>Angewandte Chemie International Edition</title><description>Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.</description><subject>Bonding</subject><subject>Congeners</subject><subject>Forges</subject><subject>Formations</subject><subject>Quinones</subject><subject>Series (mathematics)</subject><subject>Strategy</subject><subject>Synthesis</subject><subject>Trimers</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpdjs1Kw0AUhQdRsFa3rgNu6iJ17tz5ixspRa1QEbG6DbfJ1E6JM7WTLPpYvoJPZkBXrs534ONwGDsHPgbOxRUF78aCg-TCKnvABqAE5GgMHvYsEXNjFRyzk5Q2vW8t1wN2M6NdcCn58J49dz7E4LJH16597dJ1togtNdnLPrRrl3zK4iobfX9d5m_U-opCbCan7GhFTXJnfzlkr3e3i-ksnz_dP0wn83wLCG1eWaq1JCBlepIolkXlKq1JQ933lTKyIotaGKOl4Lh0VKAoFJdCWlNYHLLR7-52Fz87l9ryw6fKNQ0FF7tUguEAHAqlevXin7qJ3S7070pQaDRagxJ_AHztWBs</recordid><startdate>20140623</startdate><enddate>20140623</enddate><creator>Jepsen, Tue H</creator><creator>Thomas, Stephen B</creator><creator>Lin, Yunqing</creator><creator>Stathakis, Christos I</creator><creator>deMiguel, Irene</creator><creator>Snyder, Scott A</creator><general>Wiley Subscription Services, Inc</general><scope>7TM</scope><scope>K9.</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140623</creationdate><title>Harnessing Quinone Methides: Total Synthesis of (±)-VaticanolA</title><author>Jepsen, Tue H ; Thomas, Stephen B ; Lin, Yunqing ; Stathakis, Christos I ; deMiguel, Irene ; Snyder, Scott A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p131t-c8ad64a1a578ad432b9cec66a61dad4f574ca83627764203bea93295042487983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Bonding</topic><topic>Congeners</topic><topic>Forges</topic><topic>Formations</topic><topic>Quinones</topic><topic>Series (mathematics)</topic><topic>Strategy</topic><topic>Synthesis</topic><topic>Trimers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jepsen, Tue H</creatorcontrib><creatorcontrib>Thomas, Stephen B</creatorcontrib><creatorcontrib>Lin, Yunqing</creatorcontrib><creatorcontrib>Stathakis, Christos I</creatorcontrib><creatorcontrib>deMiguel, Irene</creatorcontrib><creatorcontrib>Snyder, Scott A</creatorcontrib><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jepsen, Tue H</au><au>Thomas, Stephen B</au><au>Lin, Yunqing</au><au>Stathakis, Christos I</au><au>deMiguel, Irene</au><au>Snyder, Scott A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Harnessing Quinone Methides: Total Synthesis of (±)-VaticanolA</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2014-06-23</date><risdate>2014</risdate><volume>53</volume><issue>26</issue><spage>6747</spage><epage>6751</epage><pages>6747-6751</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.201402858</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record>
fulltext	fulltext
identifier	ISSN: 1433-7851
ispartof	Angewandte Chemie International Edition, 2014-06, Vol.53 (26), p.6747-6751
issn	1433-7851 1521-3773
language	eng
recordid	cdi_proquest_miscellaneous_1701101955
source	Access via Wiley Online Library
subjects	Bonding Congeners Forges Formations Quinones Series (mathematics) Strategy Synthesis Trimers
title	Harnessing Quinone Methides: Total Synthesis of (±)-VaticanolA
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-14T21%3A12%3A45IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Harnessing%20Quinone%20Methides:%20Total%20Synthesis%20of%20(%C2%B1)-VaticanolA&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Jepsen,%20Tue%20H&rft.date=2014-06-23&rft.volume=53&rft.issue=26&rft.spage=6747&rft.epage=6751&rft.pages=6747-6751&rft.issn=1433-7851&rft.eissn=1521-3773&rft.coden=ACIEAY&rft_id=info:doi/10.1002/anie.201402858&rft_dat=%3Cproquest%3E1701101955%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1537638734&rft_id=info:pmid/&rfr_iscdi=true