The Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one via Prins Cyclization
The stereoselective total synthesis of an antiproliferative and antifungal α‐pyrone natural product (6S)‐5,6‐dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and ring‐closing metathesis reaction....
Gespeichert in:
Veröffentlicht in: | Helvetica chimica acta 2010-07, Vol.93 (7), p.1432-1438 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 1438 |
---|---|
container_issue | 7 |
container_start_page | 1432 |
container_title | Helvetica chimica acta |
container_volume | 93 |
creator | Yadav, Jhillu Singh Chandrakanth, Dandekar Rao, Yerragorla Gopala Ravindar, Kontham Reddy, Basi V. Subba |
description | The stereoselective total synthesis of an antiproliferative and antifungal α‐pyrone natural product (6S)‐5,6‐dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and ring‐closing metathesis reaction. |
doi_str_mv | 10.1002/hlca.200900414 |
format | Article |
fullrecord | <record><control><sourceid>wiley_istex</sourceid><recordid>TN_cdi_wiley_primary_10_1002_hlca_200900414_HLCA200900414</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>HLCA200900414</sourcerecordid><originalsourceid>FETCH-LOGICAL-i2434-dc5ba936b1f5a480245c39029273536ef4f289ba4c9f5d251116fcaa558fec743</originalsourceid><addsrcrecordid>eNo9kM9LwzAYhoMoOKdXzz1uYGZ-ts1xVN1kY4qrTBAJWZbSaGxHW-Yi-L_bOdnp4_14n_fwAHCJ0QAjRK5zp9WAICQQYpgdgQ7mhEASRvwYdBDCMURYvJyCs7p-R21NoKgDftLcBPPGVKasjTO6sRsTpGWjXDD3RZOb2tZBmQW9cN6H_CqENzb3q6qEIXztkac-JPAvb337Weem8C43W-_eIBnDta9U0TbKwgQbq4LHyhZ1kHjt7LdqbFmcg5NMudpc_N8ueL67TZMxnD6M7pPhFFrCKIMrzZdK0HCJM65YjAjjmgpEBIkop6HJWEZisVRMi4yvCMcYh5lWivM4MzpitAvEfvfLOuPlurKfqvISI7kzJ3fm5MGcHE-T4SG1LNyztm7M9sCq6kOGEY24XMxGEo0W6WRGYzmhv82DcrA</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>The Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one via Prins Cyclization</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Yadav, Jhillu Singh ; Chandrakanth, Dandekar ; Rao, Yerragorla Gopala ; Ravindar, Kontham ; Reddy, Basi V. Subba</creator><creatorcontrib>Yadav, Jhillu Singh ; Chandrakanth, Dandekar ; Rao, Yerragorla Gopala ; Ravindar, Kontham ; Reddy, Basi V. Subba</creatorcontrib><description>The stereoselective total synthesis of an antiproliferative and antifungal α‐pyrone natural product (6S)‐5,6‐dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and ring‐closing metathesis reaction.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.200900414</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>2H-Pyran-2-ones ; Mitsunobu reaction ; Prins cyclization ; Ring-closing metathesis (RCM)</subject><ispartof>Helvetica chimica acta, 2010-07, Vol.93 (7), p.1432-1438</ispartof><rights>Copyright © 2010 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></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.200900414$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.200900414$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Yadav, Jhillu Singh</creatorcontrib><creatorcontrib>Chandrakanth, Dandekar</creatorcontrib><creatorcontrib>Rao, Yerragorla Gopala</creatorcontrib><creatorcontrib>Ravindar, Kontham</creatorcontrib><creatorcontrib>Reddy, Basi V. Subba</creatorcontrib><title>The Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one via Prins Cyclization</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>The stereoselective total synthesis of an antiproliferative and antifungal α‐pyrone natural product (6S)‐5,6‐dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and ring‐closing metathesis reaction.</description><subject>2H-Pyran-2-ones</subject><subject>Mitsunobu reaction</subject><subject>Prins cyclization</subject><subject>Ring-closing metathesis (RCM)</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNo9kM9LwzAYhoMoOKdXzz1uYGZ-ts1xVN1kY4qrTBAJWZbSaGxHW-Yi-L_bOdnp4_14n_fwAHCJ0QAjRK5zp9WAICQQYpgdgQ7mhEASRvwYdBDCMURYvJyCs7p-R21NoKgDftLcBPPGVKasjTO6sRsTpGWjXDD3RZOb2tZBmQW9cN6H_CqENzb3q6qEIXztkac-JPAvb337Weem8C43W-_eIBnDta9U0TbKwgQbq4LHyhZ1kHjt7LdqbFmcg5NMudpc_N8ueL67TZMxnD6M7pPhFFrCKIMrzZdK0HCJM65YjAjjmgpEBIkop6HJWEZisVRMi4yvCMcYh5lWivM4MzpitAvEfvfLOuPlurKfqvISI7kzJ3fm5MGcHE-T4SG1LNyztm7M9sCq6kOGEY24XMxGEo0W6WRGYzmhv82DcrA</recordid><startdate>201007</startdate><enddate>201007</enddate><creator>Yadav, Jhillu Singh</creator><creator>Chandrakanth, Dandekar</creator><creator>Rao, Yerragorla Gopala</creator><creator>Ravindar, Kontham</creator><creator>Reddy, Basi V. Subba</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope></search><sort><creationdate>201007</creationdate><title>The Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one via Prins Cyclization</title><author>Yadav, Jhillu Singh ; Chandrakanth, Dandekar ; Rao, Yerragorla Gopala ; Ravindar, Kontham ; Reddy, Basi V. Subba</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i2434-dc5ba936b1f5a480245c39029273536ef4f289ba4c9f5d251116fcaa558fec743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>2H-Pyran-2-ones</topic><topic>Mitsunobu reaction</topic><topic>Prins cyclization</topic><topic>Ring-closing metathesis (RCM)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yadav, Jhillu Singh</creatorcontrib><creatorcontrib>Chandrakanth, Dandekar</creatorcontrib><creatorcontrib>Rao, Yerragorla Gopala</creatorcontrib><creatorcontrib>Ravindar, Kontham</creatorcontrib><creatorcontrib>Reddy, Basi V. Subba</creatorcontrib><collection>Istex</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yadav, Jhillu Singh</au><au>Chandrakanth, Dandekar</au><au>Rao, Yerragorla Gopala</au><au>Ravindar, Kontham</au><au>Reddy, Basi V. Subba</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one via Prins Cyclization</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>2010-07</date><risdate>2010</risdate><volume>93</volume><issue>7</issue><spage>1432</spage><epage>1438</epage><pages>1432-1438</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>The stereoselective total synthesis of an antiproliferative and antifungal α‐pyrone natural product (6S)‐5,6‐dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and ring‐closing metathesis reaction.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/hlca.200900414</doi><tpages>7</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0018-019X |
ispartof | Helvetica chimica acta, 2010-07, Vol.93 (7), p.1432-1438 |
issn | 0018-019X 1522-2675 |
language | eng |
recordid | cdi_wiley_primary_10_1002_hlca_200900414_HLCA200900414 |
source | Wiley Online Library Journals Frontfile Complete |
subjects | 2H-Pyran-2-ones Mitsunobu reaction Prins cyclization Ring-closing metathesis (RCM) |
title | The Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one via Prins Cyclization |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T19%3A40%3A19IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_istex&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20Stereoselective%20Total%20Synthesis%20of%20(6S)-5,6-Dihydro-6-%5B(2R)-2-hydroxy-6-phenylhexyl%5D-2H-pyran-2-one%20via%20Prins%20Cyclization&rft.jtitle=Helvetica%20chimica%20acta&rft.au=Yadav,%20Jhillu%E2%80%85Singh&rft.date=2010-07&rft.volume=93&rft.issue=7&rft.spage=1432&rft.epage=1438&rft.pages=1432-1438&rft.issn=0018-019X&rft.eissn=1522-2675&rft_id=info:doi/10.1002/hlca.200900414&rft_dat=%3Cwiley_istex%3EHLCA200900414%3C/wiley_istex%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 |