Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives

The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydrox...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2003-10, Vol.68 (20), p.7779-7787
Main Authors: Carreño, M. Carmen, Des Mazery, Renaud, Urbano, Antonio, Colobert, Françoise, Solladié, Guy
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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-a445t-ef0c859bf5c7d8dc46fdf81bfe33f42d9e963162b6b2869c9a647b335d8f0b5c3
cites cdi_FETCH-LOGICAL-a445t-ef0c859bf5c7d8dc46fdf81bfe33f42d9e963162b6b2869c9a647b335d8f0b5c3
container_end_page 7787
container_issue 20
container_start_page 7779
container_title Journal of organic chemistry
container_volume 68
creator Carreño, M. Carmen
Des Mazery, Renaud
Urbano, Antonio
Colobert, Françoise
Solladié, Guy
description The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (−)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).
doi_str_mv 10.1021/jo034817x
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_75711645</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>75711645</sourcerecordid><originalsourceid>FETCH-LOGICAL-a445t-ef0c859bf5c7d8dc46fdf81bfe33f42d9e963162b6b2869c9a647b335d8f0b5c3</originalsourceid><addsrcrecordid>eNptkM9u1DAQxi0EokvhwAugXEDikNZ_YifhVi1tt2IFiC5ny7HHIiWbbD1JtempV16zT4KjXXU54MtYM7_v08xHyFtGTxjl7PSmoyIrWL59RmZMcpqqkmbPyYxSzlPBlTgirxBvaHxSypfkiGWSTd8ZefgBbrB9fQfJfLRNfW_6umsx6XyyGF3otiMOja_bsUm-QN-1gJ8eH_4k561pI4jQwE58Zi0gJn2XrKAP5tek3YzBtIlp3T89P0y9zxDqOzMJ8TV54U2D8GZfj8nPi_PVfJEuv11ezc-Wqcky2afgqS1kWXlpc1c4mynvfMEqD0L4jLsSSiWY4pWqeKFKWxqV5ZUQ0hWeVtKKY_Jh57sJ3e0A2Ot1jRaaxrTQDahzmTOmMhnBjzvQhg4xgNebUK9NGDWjeopbP8Ud2Xd706FagzuQ-3wj8H4PGLSm8fF4W-OBk0wVkuWRS3dcjT1sn-Ym_NYqF7nUq-_Xep5fXy4XvNRfD77GYtxnCG3M7j8L_gUmGaep</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>75711645</pqid></control><display><type>article</type><title>Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Carreño, M. Carmen ; Des Mazery, Renaud ; Urbano, Antonio ; Colobert, Françoise ; Solladié, Guy</creator><creatorcontrib>Carreño, M. Carmen ; Des Mazery, Renaud ; Urbano, Antonio ; Colobert, Françoise ; Solladié, Guy</creatorcontrib><description>The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (−)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo034817x</identifier><identifier>PMID: 14510555</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2003-10, Vol.68 (20), p.7779-7787</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-ef0c859bf5c7d8dc46fdf81bfe33f42d9e963162b6b2869c9a647b335d8f0b5c3</citedby><cites>FETCH-LOGICAL-a445t-ef0c859bf5c7d8dc46fdf81bfe33f42d9e963162b6b2869c9a647b335d8f0b5c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=15168517$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14510555$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Carreño, M. Carmen</creatorcontrib><creatorcontrib>Des Mazery, Renaud</creatorcontrib><creatorcontrib>Urbano, Antonio</creatorcontrib><creatorcontrib>Colobert, Françoise</creatorcontrib><creatorcontrib>Solladié, Guy</creatorcontrib><title>Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (−)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNptkM9u1DAQxi0EokvhwAugXEDikNZ_YifhVi1tt2IFiC5ny7HHIiWbbD1JtempV16zT4KjXXU54MtYM7_v08xHyFtGTxjl7PSmoyIrWL59RmZMcpqqkmbPyYxSzlPBlTgirxBvaHxSypfkiGWSTd8ZefgBbrB9fQfJfLRNfW_6umsx6XyyGF3otiMOja_bsUm-QN-1gJ8eH_4k561pI4jQwE58Zi0gJn2XrKAP5tek3YzBtIlp3T89P0y9zxDqOzMJ8TV54U2D8GZfj8nPi_PVfJEuv11ezc-Wqcky2afgqS1kWXlpc1c4mynvfMEqD0L4jLsSSiWY4pWqeKFKWxqV5ZUQ0hWeVtKKY_Jh57sJ3e0A2Ot1jRaaxrTQDahzmTOmMhnBjzvQhg4xgNebUK9NGDWjeopbP8Ud2Xd706FagzuQ-3wj8H4PGLSm8fF4W-OBk0wVkuWRS3dcjT1sn-Ym_NYqF7nUq-_Xep5fXy4XvNRfD77GYtxnCG3M7j8L_gUmGaep</recordid><startdate>20031003</startdate><enddate>20031003</enddate><creator>Carreño, M. Carmen</creator><creator>Des Mazery, Renaud</creator><creator>Urbano, Antonio</creator><creator>Colobert, Françoise</creator><creator>Solladié, Guy</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20031003</creationdate><title>Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives</title><author>Carreño, M. Carmen ; Des Mazery, Renaud ; Urbano, Antonio ; Colobert, Françoise ; Solladié, Guy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-ef0c859bf5c7d8dc46fdf81bfe33f42d9e963162b6b2869c9a647b335d8f0b5c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Carreño, M. Carmen</creatorcontrib><creatorcontrib>Des Mazery, Renaud</creatorcontrib><creatorcontrib>Urbano, Antonio</creatorcontrib><creatorcontrib>Colobert, Françoise</creatorcontrib><creatorcontrib>Solladié, Guy</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Carreño, M. Carmen</au><au>Des Mazery, Renaud</au><au>Urbano, Antonio</au><au>Colobert, Françoise</au><au>Solladié, Guy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-10-03</date><risdate>2003</risdate><volume>68</volume><issue>20</issue><spage>7779</spage><epage>7787</epage><pages>7779-7787</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (−)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14510555</pmid><doi>10.1021/jo034817x</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2003-10, Vol.68 (20), p.7779-7787
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_75711645
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
title Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T10%3A51%3A29IST&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=Reductive%20Cyclizations%20of%20Hydroxysulfinyl%20Ketones:%E2%80%89%20Enantioselective%20Access%20to%20Tetrahydropyran%20and%20Tetrahydrofuran%20Derivatives&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Carre%C3%B1o,%20M.%20Carmen&rft.date=2003-10-03&rft.volume=68&rft.issue=20&rft.spage=7779&rft.epage=7787&rft.pages=7779-7787&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo034817x&rft_dat=%3Cproquest_cross%3E75711645%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a445t-ef0c859bf5c7d8dc46fdf81bfe33f42d9e963162b6b2869c9a647b335d8f0b5c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=75711645&rft_id=info:pmid/14510555&rfr_iscdi=true