Stereo- and Regioselective Glycosylations to the Bis-C-arylglycoside of Kidamycin

In explorations toward the total synthesis of the antitumor anthrapyran natural product kidamycin, the regioselective introduction of aminosugars angolosamine and vancosamine as C-arylglycosides has been accomplished onto hydroxylated anthrapyran aglycones. Specifically, the 9,11-dihydroxylated anth...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2007-08, Vol.9 (18), p.3547-3550
Hauptverfasser:	Fei, ZhongBo, McDonald, Frank E
Format:	Artikel
Sprache:	eng
Schlagworte:	Aminoglycosides - chemistry Antineoplastic Agents - chemistry Glycosides - chemistry Glycosylation Molecular Structure Stereoisomerism
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	3550
container_issue	18
container_start_page	3547
container_title	Organic letters
container_volume	9
creator	Fei, ZhongBo McDonald, Frank E
description	In explorations toward the total synthesis of the antitumor anthrapyran natural product kidamycin, the regioselective introduction of aminosugars angolosamine and vancosamine as C-arylglycosides has been accomplished onto hydroxylated anthrapyran aglycones. Specifically, the 9,11-dihydroxylated anthrapyran A undergoes sequential glycosylations with angolosamine synthon B and vancosamine synthon C to regio- and stereoselectively afford bis-C-glycoside D corresponding to the C-glycoside pattern of kidamycin.
doi_str_mv	10.1021/ol7014219
format	Article
fullrecord	<record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4604443</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68194648</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-54a47320d6c28a0d78c2668f5198b3e7a22869eb967553aeb9c63aa51034400b3</originalsourceid><addsrcrecordid>eNptkU1Lw0AQhhdRbK0e_AOSi4KH6H5lk1wELVrFgvh1XjabSbtlk63ZpJB_b7SlKnial5mHd15mEDom-IJgSi6djTHhlKQ7aEgiysIYR3R3qwUeoAPvFxiTvpPuowGJRUriNBmi59cGanBhoKo8eIGZcR4s6MasIJjYTjvfWdUYV_mgcUEzh-DG-HAcqrqzs--5ySFwRfBoclV22lSHaK9Q1sPRpo7Q-93t2_g-nD5NHsbX01Axxpow4orHjOJcaJoonMeJpkIkRUTSJGMQK0oTkUKWijiKmOqFFkypiGDGOcYZG6Grte-yzUrINVRNraxc1qbsw0mnjPw7qcxcztxKcoE556w3ONsY1O6jBd_I0ngN1qoKXOulSEjKBU968HwN6tp5X0OxXUKw_HqA3D6gZ09-p_ohNxfvgdM1oLSXC9fWVX-kf4w-ATrCjKM</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68194648</pqid></control><display><type>article</type><title>Stereo- and Regioselective Glycosylations to the Bis-C-arylglycoside of Kidamycin</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Fei, ZhongBo ; McDonald, Frank E</creator><creatorcontrib>Fei, ZhongBo ; McDonald, Frank E</creatorcontrib><description>In explorations toward the total synthesis of the antitumor anthrapyran natural product kidamycin, the regioselective introduction of aminosugars angolosamine and vancosamine as C-arylglycosides has been accomplished onto hydroxylated anthrapyran aglycones. Specifically, the 9,11-dihydroxylated anthrapyran A undergoes sequential glycosylations with angolosamine synthon B and vancosamine synthon C to regio- and stereoselectively afford bis-C-glycoside D corresponding to the C-glycoside pattern of kidamycin.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol7014219</identifier><identifier>PMID: 17691798</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aminoglycosides - chemistry ; Antineoplastic Agents - chemistry ; Glycosides - chemistry ; Glycosylation ; Molecular Structure ; Stereoisomerism</subject><ispartof>Organic letters, 2007-08, Vol.9 (18), p.3547-3550</ispartof><rights>Copyright © 2007 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-54a47320d6c28a0d78c2668f5198b3e7a22869eb967553aeb9c63aa51034400b3</citedby><cites>FETCH-LOGICAL-a333t-54a47320d6c28a0d78c2668f5198b3e7a22869eb967553aeb9c63aa51034400b3</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/ol7014219$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol7014219$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17691798$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fei, ZhongBo</creatorcontrib><creatorcontrib>McDonald, Frank E</creatorcontrib><title>Stereo- and Regioselective Glycosylations to the Bis-C-arylglycoside of Kidamycin</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>In explorations toward the total synthesis of the antitumor anthrapyran natural product kidamycin, the regioselective introduction of aminosugars angolosamine and vancosamine as C-arylglycosides has been accomplished onto hydroxylated anthrapyran aglycones. Specifically, the 9,11-dihydroxylated anthrapyran A undergoes sequential glycosylations with angolosamine synthon B and vancosamine synthon C to regio- and stereoselectively afford bis-C-glycoside D corresponding to the C-glycoside pattern of kidamycin.</description><subject>Aminoglycosides - chemistry</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Glycosides - chemistry</subject><subject>Glycosylation</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU1Lw0AQhhdRbK0e_AOSi4KH6H5lk1wELVrFgvh1XjabSbtlk63ZpJB_b7SlKnial5mHd15mEDom-IJgSi6djTHhlKQ7aEgiysIYR3R3qwUeoAPvFxiTvpPuowGJRUriNBmi59cGanBhoKo8eIGZcR4s6MasIJjYTjvfWdUYV_mgcUEzh-DG-HAcqrqzs--5ySFwRfBoclV22lSHaK9Q1sPRpo7Q-93t2_g-nD5NHsbX01Axxpow4orHjOJcaJoonMeJpkIkRUTSJGMQK0oTkUKWijiKmOqFFkypiGDGOcYZG6Grte-yzUrINVRNraxc1qbsw0mnjPw7qcxcztxKcoE556w3ONsY1O6jBd_I0ngN1qoKXOulSEjKBU968HwN6tp5X0OxXUKw_HqA3D6gZ09-p_ohNxfvgdM1oLSXC9fWVX-kf4w-ATrCjKM</recordid><startdate>20070830</startdate><enddate>20070830</enddate><creator>Fei, ZhongBo</creator><creator>McDonald, Frank E</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><scope>5PM</scope></search><sort><creationdate>20070830</creationdate><title>Stereo- and Regioselective Glycosylations to the Bis-C-arylglycoside of Kidamycin</title><author>Fei, ZhongBo ; McDonald, Frank E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-54a47320d6c28a0d78c2668f5198b3e7a22869eb967553aeb9c63aa51034400b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Aminoglycosides - chemistry</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Glycosides - chemistry</topic><topic>Glycosylation</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fei, ZhongBo</creatorcontrib><creatorcontrib>McDonald, Frank E</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fei, ZhongBo</au><au>McDonald, Frank E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereo- and Regioselective Glycosylations to the Bis-C-arylglycoside of Kidamycin</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2007-08-30</date><risdate>2007</risdate><volume>9</volume><issue>18</issue><spage>3547</spage><epage>3550</epage><pages>3547-3550</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>In explorations toward the total synthesis of the antitumor anthrapyran natural product kidamycin, the regioselective introduction of aminosugars angolosamine and vancosamine as C-arylglycosides has been accomplished onto hydroxylated anthrapyran aglycones. Specifically, the 9,11-dihydroxylated anthrapyran A undergoes sequential glycosylations with angolosamine synthon B and vancosamine synthon C to regio- and stereoselectively afford bis-C-glycoside D corresponding to the C-glycoside pattern of kidamycin.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>17691798</pmid><doi>10.1021/ol7014219</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7060
ispartof	Organic letters, 2007-08, Vol.9 (18), p.3547-3550
issn	1523-7060 1523-7052
language	eng
recordid	cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4604443
source	MEDLINE; American Chemical Society Journals
subjects	Aminoglycosides - chemistry Antineoplastic Agents - chemistry Glycosides - chemistry Glycosylation Molecular Structure Stereoisomerism
title	Stereo- and Regioselective Glycosylations to the Bis-C-arylglycoside of Kidamycin
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T13%3A36%3A04IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Stereo-%20and%20Regioselective%20Glycosylations%20to%20the%20Bis-C-arylglycoside%20of%20Kidamycin&rft.jtitle=Organic%20letters&rft.au=Fei,%20ZhongBo&rft.date=2007-08-30&rft.volume=9&rft.issue=18&rft.spage=3547&rft.epage=3550&rft.pages=3547-3550&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol7014219&rft_dat=%3Cproquest_pubme%3E68194648%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=68194648&rft_id=info:pmid/17691798&rfr_iscdi=true