Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene

Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene

A new synthetic method for cycloheptanone derivatives was developed on the basis of a novel [5 + 2] cycloaddition reaction using a dicobalt hexacarbonyl propargyl cation species and a silyloxyallene. The method can be applied for constructing functionalized hydroazulene skeletons, and a total synthe...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry letters 2010-06, Vol.39 (6), p.630-632
Hauptverfasser: Mitachi, Katsuhiko, Yamamoto, Takashi, Kondo, Fumikatsu, Shimizu, Tadashi, Miyashita, Masaaki, Tanino, Keiji
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 632
container_issue 6
container_start_page 630
container_title Chemistry letters
container_volume 39
creator Mitachi, Katsuhiko
Yamamoto, Takashi
Kondo, Fumikatsu
Shimizu, Tadashi
Miyashita, Masaaki
Tanino, Keiji
description A new synthetic method for cycloheptanone derivatives was developed on the basis of a novel [5 + 2] cycloaddition reaction using a dicobalt hexacarbonyl propargyl cation species and a silyloxyallene. The method can be applied for constructing functionalized hydroazulene skeletons, and a total synthesis of sesquiterpene furanether B was achieved through the reactions involving transformation of the dicobalt acetylene complex into a maleic anhydride derivative and the crucial oxidative transannular ether ring formation.
doi_str_mv 10.1246/cl.2010.630
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1461025744</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3135451751</sourcerecordid><originalsourceid>FETCH-LOGICAL-c420t-467bfecff8743b993b96b9f25520b495bed6dce2165ab77b8c221d0500ad3c413</originalsourceid><addsrcrecordid>eNptkFFLwzAUhYMoOKdP_oGAj6MzSdO0fdThnDAU3HwSCWmassysmUk7rO_-b1Md4oMPl8vlnPNdOACcYzTGhLJLacYEhYPF6AAMcEyzCKU4OQQDFDMWpYiQY3Di_RohlOUxGYDPpW2EgYuublbKaw9tBaetE7UKt4PXYzixtW9cKxtt614VcNaVzoqP1qhawcWrMqoJ0k6LoN3bnTLwOYEjSF7gpJPGirLU3-FHJX4pC206Y987YXrKKTiqhPHqbL-H4Gl6s5zMovnD7d3kah5JSlATUZYWlZJVlaU0LvI8DCvyiiQJQQXNk0KVrJSKYJaIIk2LTBKCS5QgJMpYUhwPwcUPd-vsW6t8w9e2dXV4yTFlGJEkpTS4Rj8u6az3TlV86_RGuI5jxPueuTS875mHnoM727tXaqNlYFmpVdOtxVbUf_j_RL8AoP6EGA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1461025744</pqid></control><display><type>article</type><title>Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene</title><source>Oxford University Press Journals All Titles (1996-Current)</source><creator>Mitachi, Katsuhiko ; Yamamoto, Takashi ; Kondo, Fumikatsu ; Shimizu, Tadashi ; Miyashita, Masaaki ; Tanino, Keiji</creator><creatorcontrib>Mitachi, Katsuhiko ; Yamamoto, Takashi ; Kondo, Fumikatsu ; Shimizu, Tadashi ; Miyashita, Masaaki ; Tanino, Keiji</creatorcontrib><description>A new synthetic method for cycloheptanone derivatives was developed on the basis of a novel [5 + 2] cycloaddition reaction using a dicobalt hexacarbonyl propargyl cation species and a silyloxyallene. The method can be applied for constructing functionalized hydroazulene skeletons, and a total synthesis of sesquiterpene furanether B was achieved through the reactions involving transformation of the dicobalt acetylene complex into a maleic anhydride derivative and the crucial oxidative transannular ether ring formation.</description><identifier>ISSN: 0366-7022</identifier><identifier>EISSN: 1348-0715</identifier><identifier>DOI: 10.1246/cl.2010.630</identifier><language>eng</language><publisher>Tokyo: The Chemical Society of Japan</publisher><ispartof>Chemistry letters, 2010-06, Vol.39 (6), p.630-632</ispartof><rights>The Chemical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c420t-467bfecff8743b993b96b9f25520b495bed6dce2165ab77b8c221d0500ad3c413</citedby><cites>FETCH-LOGICAL-c420t-467bfecff8743b993b96b9f25520b495bed6dce2165ab77b8c221d0500ad3c413</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></links><search><creatorcontrib>Mitachi, Katsuhiko</creatorcontrib><creatorcontrib>Yamamoto, Takashi</creatorcontrib><creatorcontrib>Kondo, Fumikatsu</creatorcontrib><creatorcontrib>Shimizu, Tadashi</creatorcontrib><creatorcontrib>Miyashita, Masaaki</creatorcontrib><creatorcontrib>Tanino, Keiji</creatorcontrib><title>Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene</title><title>Chemistry letters</title><addtitle>Chemistry Letters</addtitle><description>A new synthetic method for cycloheptanone derivatives was developed on the basis of a novel [5 + 2] cycloaddition reaction using a dicobalt hexacarbonyl propargyl cation species and a silyloxyallene. The method can be applied for constructing functionalized hydroazulene skeletons, and a total synthesis of sesquiterpene furanether B was achieved through the reactions involving transformation of the dicobalt acetylene complex into a maleic anhydride derivative and the crucial oxidative transannular ether ring formation.</description><issn>0366-7022</issn><issn>1348-0715</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNptkFFLwzAUhYMoOKdP_oGAj6MzSdO0fdThnDAU3HwSCWmassysmUk7rO_-b1Md4oMPl8vlnPNdOACcYzTGhLJLacYEhYPF6AAMcEyzCKU4OQQDFDMWpYiQY3Di_RohlOUxGYDPpW2EgYuublbKaw9tBaetE7UKt4PXYzixtW9cKxtt614VcNaVzoqP1qhawcWrMqoJ0k6LoN3bnTLwOYEjSF7gpJPGirLU3-FHJX4pC206Y987YXrKKTiqhPHqbL-H4Gl6s5zMovnD7d3kah5JSlATUZYWlZJVlaU0LvI8DCvyiiQJQQXNk0KVrJSKYJaIIk2LTBKCS5QgJMpYUhwPwcUPd-vsW6t8w9e2dXV4yTFlGJEkpTS4Rj8u6az3TlV86_RGuI5jxPueuTS875mHnoM727tXaqNlYFmpVdOtxVbUf_j_RL8AoP6EGA</recordid><startdate>20100605</startdate><enddate>20100605</enddate><creator>Mitachi, Katsuhiko</creator><creator>Yamamoto, Takashi</creator><creator>Kondo, Fumikatsu</creator><creator>Shimizu, Tadashi</creator><creator>Miyashita, Masaaki</creator><creator>Tanino, Keiji</creator><general>The Chemical Society of Japan</general><general>Chemical Society of Japan</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20100605</creationdate><title>Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene</title><author>Mitachi, Katsuhiko ; Yamamoto, Takashi ; Kondo, Fumikatsu ; Shimizu, Tadashi ; Miyashita, Masaaki ; Tanino, Keiji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c420t-467bfecff8743b993b96b9f25520b495bed6dce2165ab77b8c221d0500ad3c413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mitachi, Katsuhiko</creatorcontrib><creatorcontrib>Yamamoto, Takashi</creatorcontrib><creatorcontrib>Kondo, Fumikatsu</creatorcontrib><creatorcontrib>Shimizu, Tadashi</creatorcontrib><creatorcontrib>Miyashita, Masaaki</creatorcontrib><creatorcontrib>Tanino, Keiji</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mitachi, Katsuhiko</au><au>Yamamoto, Takashi</au><au>Kondo, Fumikatsu</au><au>Shimizu, Tadashi</au><au>Miyashita, Masaaki</au><au>Tanino, Keiji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene</atitle><jtitle>Chemistry letters</jtitle><addtitle>Chemistry Letters</addtitle><date>2010-06-05</date><risdate>2010</risdate><volume>39</volume><issue>6</issue><spage>630</spage><epage>632</epage><pages>630-632</pages><issn>0366-7022</issn><eissn>1348-0715</eissn><abstract>A new synthetic method for cycloheptanone derivatives was developed on the basis of a novel [5 + 2] cycloaddition reaction using a dicobalt hexacarbonyl propargyl cation species and a silyloxyallene. The method can be applied for constructing functionalized hydroazulene skeletons, and a total synthesis of sesquiterpene furanether B was achieved through the reactions involving transformation of the dicobalt acetylene complex into a maleic anhydride derivative and the crucial oxidative transannular ether ring formation.</abstract><cop>Tokyo</cop><pub>The Chemical Society of Japan</pub><doi>10.1246/cl.2010.630</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0366-7022
ispartof Chemistry letters, 2010-06, Vol.39 (6), p.630-632
issn 0366-7022
1348-0715
language eng
recordid cdi_proquest_journals_1461025744
source Oxford University Press Journals All Titles (1996-Current)
title Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T00%3A35%3A28IST&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=Total%20Synthesis%20of%20Furanether%20B.%20Construction%20of%20a%20Hydroazulene%20Skeleton%20via%20a%20Novel%20%5B5%20+%202%5D%20Cycloaddition%20Reaction%20of%20Silyloxyallene&rft.jtitle=Chemistry%20letters&rft.au=Mitachi,%20Katsuhiko&rft.date=2010-06-05&rft.volume=39&rft.issue=6&rft.spage=630&rft.epage=632&rft.pages=630-632&rft.issn=0366-7022&rft.eissn=1348-0715&rft_id=info:doi/10.1246/cl.2010.630&rft_dat=%3Cproquest_cross%3E3135451751%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1461025744&rft_id=info:pmid/&rfr_iscdi=true