A Stereodivergent Approach to 5a-Carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose Pentaacetates from D-Mannose, Based on 6-exo-dig Radical Cyclization and Barton−McCombie Radical Deoxygenation

The three carbasugars, 5a‐carba‐α‐D‐gluco‐, ‐α‐D‐galacto and ‐β‐L‐gulopyranose pentaacetates 42, 35 and 28 respectively, have been prepared in a stereodivergent manner from D‐mannose. Alkynyl derivatives of 2,3:4,6‐di‐O‐isopropylidene‐D‐mannopyranose, which are homologated at C‐1 by reaction with tr...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2004-04, Vol.2004 (8), p.1830-1840
Main Authors: Gómez, Ana M., Moreno, Eduardo, Valverde, Serafín, López, J. Cristóbal
Format: Article
Language:English
Subjects:
Carbohydrates
D-Mannose
Radical cyclization
Radical deoxygenation
Synthesis design
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c3259-fdc5114ea4d97508b80bf02c194e1852299bd6d7ed5971c5eddcb8cc56757f83
cites cdi_FETCH-LOGICAL-c3259-fdc5114ea4d97508b80bf02c194e1852299bd6d7ed5971c5eddcb8cc56757f83
container_end_page 1840
container_issue 8
container_start_page 1830
container_title European journal of organic chemistry
container_volume 2004
creator Gómez, Ana M.
Moreno, Eduardo
Valverde, Serafín
López, J. Cristóbal
description The three carbasugars, 5a‐carba‐α‐D‐gluco‐, ‐α‐D‐galacto and ‐β‐L‐gulopyranose pentaacetates 42, 35 and 28 respectively, have been prepared in a stereodivergent manner from D‐mannose. Alkynyl derivatives of 2,3:4,6‐di‐O‐isopropylidene‐D‐mannopyranose, which are homologated at C‐1 by reaction with trimethylsilylacetylide, undergo a 6‐exo‐dig radical cyclization, from a radical located at C‐5, to yield a mixture of highly functionalized exo‐methylenecyclohexanes. Ozonolysis of the exocyclic double bond in the latter generated cyclohexanones which, upon stereoselective reduction of the carbonyl moiety followed by site‐selective deoxygenation either at position C‐4 or C‐5a (parent carbohydrate numbering), afforded the title carbasugars. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
doi_str_mv 10.1002/ejoc.200300339
format article
fullrecord <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ejoc_200300339</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>EJOC200300339</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3259-fdc5114ea4d97508b80bf02c194e1852299bd6d7ed5971c5eddcb8cc56757f83</originalsourceid><addsrcrecordid>eNqFkc1u1DAUhSNUpP7Atms_QD3YSZzEy2mmHVpNKSojys66sW8Gt5l4ZKcw6ROw5k3gLdjwEDwJGaYadYdkyb4-5zu60omiY85GnLH4Dd45PYoZS4aTyBfRAWdSUpZJtje80ySlXCaf9qPDEO4YYzLL-EH0a0w-dOjRGfsF_QLbjoxXK-9AfyadIwJoCb4C-vsHndBF86AdPSFPEzSgBw-0Zvj5SWd08dC4Ve-hdQHJ-yELQGMHHQZSe7ckE3oF7UY8IacQ0BDXkozi2lFjF-QGjNXQkLLXjX2Ezg7qJvsUfOfaP9--X-nSLSuLO-cE3bofdv7nfRW9rKEJ-PrpPorm52fz8i2dXU8vyvGM6iQWktZGC85ThNTIXLCiKlhVs1hzmSIvRBxLWZnM5GiEzLkWaIyuCq1Flou8LpKjaLSN1d6F4LFWK2-X4HvFmdr0oDY9qF0PAyC3wFfbYP8ftzq7vC6fs3TL2tDheseCv1dZnuRC3b6bqtubsvjI5pdqnvwFVPuhOg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Stereodivergent Approach to 5a-Carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose Pentaacetates from D-Mannose, Based on 6-exo-dig Radical Cyclization and Barton−McCombie Radical Deoxygenation</title><source>Wiley</source><creator>Gómez, Ana M. ; Moreno, Eduardo ; Valverde, Serafín ; López, J. Cristóbal</creator><creatorcontrib>Gómez, Ana M. ; Moreno, Eduardo ; Valverde, Serafín ; López, J. Cristóbal</creatorcontrib><description>The three carbasugars, 5a‐carba‐α‐D‐gluco‐, ‐α‐D‐galacto and ‐β‐L‐gulopyranose pentaacetates 42, 35 and 28 respectively, have been prepared in a stereodivergent manner from D‐mannose. Alkynyl derivatives of 2,3:4,6‐di‐O‐isopropylidene‐D‐mannopyranose, which are homologated at C‐1 by reaction with trimethylsilylacetylide, undergo a 6‐exo‐dig radical cyclization, from a radical located at C‐5, to yield a mixture of highly functionalized exo‐methylenecyclohexanes. Ozonolysis of the exocyclic double bond in the latter generated cyclohexanones which, upon stereoselective reduction of the carbonyl moiety followed by site‐selective deoxygenation either at position C‐4 or C‐5a (parent carbohydrate numbering), afforded the title carbasugars. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200300339</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Carbohydrates ; D-Mannose ; Radical cyclization ; Radical deoxygenation ; Synthesis design</subject><ispartof>European journal of organic chemistry, 2004-04, Vol.2004 (8), p.1830-1840</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3259-fdc5114ea4d97508b80bf02c194e1852299bd6d7ed5971c5eddcb8cc56757f83</citedby><cites>FETCH-LOGICAL-c3259-fdc5114ea4d97508b80bf02c194e1852299bd6d7ed5971c5eddcb8cc56757f83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Gómez, Ana M.</creatorcontrib><creatorcontrib>Moreno, Eduardo</creatorcontrib><creatorcontrib>Valverde, Serafín</creatorcontrib><creatorcontrib>López, J. Cristóbal</creatorcontrib><title>A Stereodivergent Approach to 5a-Carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose Pentaacetates from D-Mannose, Based on 6-exo-dig Radical Cyclization and Barton−McCombie Radical Deoxygenation</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The three carbasugars, 5a‐carba‐α‐D‐gluco‐, ‐α‐D‐galacto and ‐β‐L‐gulopyranose pentaacetates 42, 35 and 28 respectively, have been prepared in a stereodivergent manner from D‐mannose. Alkynyl derivatives of 2,3:4,6‐di‐O‐isopropylidene‐D‐mannopyranose, which are homologated at C‐1 by reaction with trimethylsilylacetylide, undergo a 6‐exo‐dig radical cyclization, from a radical located at C‐5, to yield a mixture of highly functionalized exo‐methylenecyclohexanes. Ozonolysis of the exocyclic double bond in the latter generated cyclohexanones which, upon stereoselective reduction of the carbonyl moiety followed by site‐selective deoxygenation either at position C‐4 or C‐5a (parent carbohydrate numbering), afforded the title carbasugars. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)</description><subject>Carbohydrates</subject><subject>D-Mannose</subject><subject>Radical cyclization</subject><subject>Radical deoxygenation</subject><subject>Synthesis design</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkc1u1DAUhSNUpP7Atms_QD3YSZzEy2mmHVpNKSojys66sW8Gt5l4ZKcw6ROw5k3gLdjwEDwJGaYadYdkyb4-5zu60omiY85GnLH4Dd45PYoZS4aTyBfRAWdSUpZJtje80ySlXCaf9qPDEO4YYzLL-EH0a0w-dOjRGfsF_QLbjoxXK-9AfyadIwJoCb4C-vsHndBF86AdPSFPEzSgBw-0Zvj5SWd08dC4Ve-hdQHJ-yELQGMHHQZSe7ckE3oF7UY8IacQ0BDXkozi2lFjF-QGjNXQkLLXjX2Ezg7qJvsUfOfaP9--X-nSLSuLO-cE3bofdv7nfRW9rKEJ-PrpPorm52fz8i2dXU8vyvGM6iQWktZGC85ThNTIXLCiKlhVs1hzmSIvRBxLWZnM5GiEzLkWaIyuCq1Flou8LpKjaLSN1d6F4LFWK2-X4HvFmdr0oDY9qF0PAyC3wFfbYP8ftzq7vC6fs3TL2tDheseCv1dZnuRC3b6bqtubsvjI5pdqnvwFVPuhOg</recordid><startdate>200404</startdate><enddate>200404</enddate><creator>Gómez, Ana M.</creator><creator>Moreno, Eduardo</creator><creator>Valverde, Serafín</creator><creator>López, J. Cristóbal</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200404</creationdate><title>A Stereodivergent Approach to 5a-Carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose Pentaacetates from D-Mannose, Based on 6-exo-dig Radical Cyclization and Barton−McCombie Radical Deoxygenation</title><author>Gómez, Ana M. ; Moreno, Eduardo ; Valverde, Serafín ; López, J. Cristóbal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3259-fdc5114ea4d97508b80bf02c194e1852299bd6d7ed5971c5eddcb8cc56757f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Carbohydrates</topic><topic>D-Mannose</topic><topic>Radical cyclization</topic><topic>Radical deoxygenation</topic><topic>Synthesis design</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gómez, Ana M.</creatorcontrib><creatorcontrib>Moreno, Eduardo</creatorcontrib><creatorcontrib>Valverde, Serafín</creatorcontrib><creatorcontrib>López, J. Cristóbal</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gómez, Ana M.</au><au>Moreno, Eduardo</au><au>Valverde, Serafín</au><au>López, J. Cristóbal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Stereodivergent Approach to 5a-Carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose Pentaacetates from D-Mannose, Based on 6-exo-dig Radical Cyclization and Barton−McCombie Radical Deoxygenation</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2004-04</date><risdate>2004</risdate><volume>2004</volume><issue>8</issue><spage>1830</spage><epage>1840</epage><pages>1830-1840</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The three carbasugars, 5a‐carba‐α‐D‐gluco‐, ‐α‐D‐galacto and ‐β‐L‐gulopyranose pentaacetates 42, 35 and 28 respectively, have been prepared in a stereodivergent manner from D‐mannose. Alkynyl derivatives of 2,3:4,6‐di‐O‐isopropylidene‐D‐mannopyranose, which are homologated at C‐1 by reaction with trimethylsilylacetylide, undergo a 6‐exo‐dig radical cyclization, from a radical located at C‐5, to yield a mixture of highly functionalized exo‐methylenecyclohexanes. Ozonolysis of the exocyclic double bond in the latter generated cyclohexanones which, upon stereoselective reduction of the carbonyl moiety followed by site‐selective deoxygenation either at position C‐4 or C‐5a (parent carbohydrate numbering), afforded the title carbasugars. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200300339</doi><tpages>11</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European journal of organic chemistry, 2004-04, Vol.2004 (8), p.1830-1840
issn 1434-193X
1099-0690
language eng
recordid cdi_crossref_primary_10_1002_ejoc_200300339
source Wiley
subjects Carbohydrates
D-Mannose
Radical cyclization
Radical deoxygenation
Synthesis design
title A Stereodivergent Approach to 5a-Carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose Pentaacetates from D-Mannose, Based on 6-exo-dig Radical Cyclization and Barton−McCombie Radical Deoxygenation
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T21%3A15%3A22IST&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=A%20Stereodivergent%20Approach%20to%205a-Carba-%CE%B1-D-gluco-,%20-%CE%B1-D-galacto%20and%20-%CE%B2-L-gulopyranose%20Pentaacetates%20from%20D-Mannose,%20Based%20on%206-exo-dig%20Radical%20Cyclization%20and%20Barton%E2%88%92McCombie%20Radical%20Deoxygenation&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=G%C3%B3mez,%20Ana%C2%A0M.&rft.date=2004-04&rft.volume=2004&rft.issue=8&rft.spage=1830&rft.epage=1840&rft.pages=1830-1840&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.200300339&rft_dat=%3Cwiley_cross%3EEJOC200300339%3C/wiley_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3259-fdc5114ea4d97508b80bf02c194e1852299bd6d7ed5971c5eddcb8cc56757f83%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true