Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax
The enantiomers and the racemate of (3R,4S,1′E)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) were synthesized by employing Ireland's ester enolate Claisen rearrangement of 5 as the key reaction to provide the corresponding lactone 3 via 4. Optically active 3 was prepared by employing either chem...
Gespeichert in:
| Veröffentlicht in: | Liebigs Annalen der Chemie 1993-12, Vol.1993 (12), p.1287-1294 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1294 |
|---|---|
| container_issue | 12 |
| container_start_page | 1287 |
| container_title | Liebigs Annalen der Chemie |
| container_volume | 1993 |
| creator | Mori, Kenji Amaike, Masayasu Watanabe, Hidenori |
| description | The enantiomers and the racemate of (3R,4S,1′E)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) were synthesized by employing Ireland's ester enolate Claisen rearrangement of 5 as the key reaction to provide the corresponding lactone 3 via 4. Optically active 3 was prepared by employing either chemical asymmetric reduction [12 → (S)‐8b] or lipase‐mediated asymmetric hydrolysis (9→10) and acetylation (meso‐2 → ent‐10) as the key transformations. The absolute configuration of the naturally occurring 1 was revised as (3R,4S) on the basis of the chemical asymmetric synthesis of (3S,4R)‐3 by starting from (S)‐8b of known stereochemistry. |
| doi_str_mv | 10.1002/jlac.1993199301210 |
| format | Article |
| fullrecord | <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_jlac_1993199301210</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_55KZTL1G_Q</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3510-3ef28a072481282bd5df75653c282a446419daf739e88e37330990b49beeb2e43</originalsourceid><addsrcrecordid>eNqNkMtu20AMRQdBA8R18gNdzaLLyuW8LGnpCIntVkjaPFqgm8FIouxJZMmYker4W_qzleEgr1UWBMFL3kPgEvKJwYgB8K93lclHLI7FroBxBgdkwCCOAxjH8IEMgIUQcJDsiHz0_g5ASqb4gPz7sUTXrJoa6fW2bpforf9Ck_TXfD4f0QvcPMvU1AW9wr_W26amTUl7mU4y31RdizRp6tIuOmfaF9sZrqzJsTUVff7zuLte2xoLmtjWdZ6edgt6ateucV3Vj5nNzMMxOSxN5fHksQ_J7fnZTTIL0svpPJmkQS4Ug0BgySMDIZcR4xHPClWUoRorkfeTkXIsWVyYMhQxRhGKUIg-F8hknCFmHKUYEr7n5q7x3mGp186ujNtqBnoXr97Fq1_F25s-701r43NTlc7UufVPThFxFcGOPdmfbWyF23eA9bd0krx9FewZ1rf48MQw7l6PQxEq_ftiqpX6_ucmZVP9U_wH2POd-g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax</title><source>Wiley Online Library All Journals</source><creator>Mori, Kenji ; Amaike, Masayasu ; Watanabe, Hidenori</creator><creatorcontrib>Mori, Kenji ; Amaike, Masayasu ; Watanabe, Hidenori</creatorcontrib><description>The enantiomers and the racemate of (3R,4S,1′E)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) were synthesized by employing Ireland's ester enolate Claisen rearrangement of 5 as the key reaction to provide the corresponding lactone 3 via 4. Optically active 3 was prepared by employing either chemical asymmetric reduction [12 → (S)‐8b] or lipase‐mediated asymmetric hydrolysis (9→10) and acetylation (meso‐2 → ent‐10) as the key transformations. The absolute configuration of the naturally occurring 1 was revised as (3R,4S) on the basis of the chemical asymmetric synthesis of (3S,4R)‐3 by starting from (S)‐8b of known stereochemistry.</description><identifier>ISSN: 0170-2041</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/jlac.1993199301210</identifier><identifier>CODEN: LACHDL</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Biprorulus bibax ; Chemistry ; Claisen rearrangement ; Exact sciences and technology ; Hemiacetals ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Lactones ; Lipases ; Organic chemistry ; Pheromones ; Preparations and properties</subject><ispartof>Liebigs Annalen der Chemie, 1993-12, Vol.1993 (12), p.1287-1294</ispartof><rights>Copyright © 1993 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>1994 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3510-3ef28a072481282bd5df75653c282a446419daf739e88e37330990b49beeb2e43</citedby><cites>FETCH-LOGICAL-c3510-3ef28a072481282bd5df75653c282a446419daf739e88e37330990b49beeb2e43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjlac.1993199301210$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjlac.1993199301210$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3825804$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Mori, Kenji</creatorcontrib><creatorcontrib>Amaike, Masayasu</creatorcontrib><creatorcontrib>Watanabe, Hidenori</creatorcontrib><title>Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax</title><title>Liebigs Annalen der Chemie</title><addtitle>Liebigs Ann. Chem</addtitle><description>The enantiomers and the racemate of (3R,4S,1′E)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) were synthesized by employing Ireland's ester enolate Claisen rearrangement of 5 as the key reaction to provide the corresponding lactone 3 via 4. Optically active 3 was prepared by employing either chemical asymmetric reduction [12 → (S)‐8b] or lipase‐mediated asymmetric hydrolysis (9→10) and acetylation (meso‐2 → ent‐10) as the key transformations. The absolute configuration of the naturally occurring 1 was revised as (3R,4S) on the basis of the chemical asymmetric synthesis of (3S,4R)‐3 by starting from (S)‐8b of known stereochemistry.</description><subject>Biprorulus bibax</subject><subject>Chemistry</subject><subject>Claisen rearrangement</subject><subject>Exact sciences and technology</subject><subject>Hemiacetals</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Lactones</subject><subject>Lipases</subject><subject>Organic chemistry</subject><subject>Pheromones</subject><subject>Preparations and properties</subject><issn>0170-2041</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><recordid>eNqNkMtu20AMRQdBA8R18gNdzaLLyuW8LGnpCIntVkjaPFqgm8FIouxJZMmYker4W_qzleEgr1UWBMFL3kPgEvKJwYgB8K93lclHLI7FroBxBgdkwCCOAxjH8IEMgIUQcJDsiHz0_g5ASqb4gPz7sUTXrJoa6fW2bpforf9Ck_TXfD4f0QvcPMvU1AW9wr_W26amTUl7mU4y31RdizRp6tIuOmfaF9sZrqzJsTUVff7zuLte2xoLmtjWdZ6edgt6ateucV3Vj5nNzMMxOSxN5fHksQ_J7fnZTTIL0svpPJmkQS4Ug0BgySMDIZcR4xHPClWUoRorkfeTkXIsWVyYMhQxRhGKUIg-F8hknCFmHKUYEr7n5q7x3mGp186ujNtqBnoXr97Fq1_F25s-701r43NTlc7UufVPThFxFcGOPdmfbWyF23eA9bd0krx9FewZ1rf48MQw7l6PQxEq_ftiqpX6_ucmZVP9U_wH2POd-g</recordid><startdate>19931213</startdate><enddate>19931213</enddate><creator>Mori, Kenji</creator><creator>Amaike, Masayasu</creator><creator>Watanabe, Hidenori</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19931213</creationdate><title>Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax</title><author>Mori, Kenji ; Amaike, Masayasu ; Watanabe, Hidenori</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3510-3ef28a072481282bd5df75653c282a446419daf739e88e37330990b49beeb2e43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Biprorulus bibax</topic><topic>Chemistry</topic><topic>Claisen rearrangement</topic><topic>Exact sciences and technology</topic><topic>Hemiacetals</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Lactones</topic><topic>Lipases</topic><topic>Organic chemistry</topic><topic>Pheromones</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mori, Kenji</creatorcontrib><creatorcontrib>Amaike, Masayasu</creatorcontrib><creatorcontrib>Watanabe, Hidenori</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Liebigs Annalen der Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mori, Kenji</au><au>Amaike, Masayasu</au><au>Watanabe, Hidenori</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax</atitle><jtitle>Liebigs Annalen der Chemie</jtitle><addtitle>Liebigs Ann. Chem</addtitle><date>1993-12-13</date><risdate>1993</risdate><volume>1993</volume><issue>12</issue><spage>1287</spage><epage>1294</epage><pages>1287-1294</pages><issn>0170-2041</issn><eissn>1099-0690</eissn><coden>LACHDL</coden><abstract>The enantiomers and the racemate of (3R,4S,1′E)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) were synthesized by employing Ireland's ester enolate Claisen rearrangement of 5 as the key reaction to provide the corresponding lactone 3 via 4. Optically active 3 was prepared by employing either chemical asymmetric reduction [12 → (S)‐8b] or lipase‐mediated asymmetric hydrolysis (9→10) and acetylation (meso‐2 → ent‐10) as the key transformations. The absolute configuration of the naturally occurring 1 was revised as (3R,4S) on the basis of the chemical asymmetric synthesis of (3S,4R)‐3 by starting from (S)‐8b of known stereochemistry.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/jlac.1993199301210</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0170-2041 |
| ispartof | Liebigs Annalen der Chemie, 1993-12, Vol.1993 (12), p.1287-1294 |
| issn | 0170-2041 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_jlac_1993199301210 |
| source | Wiley Online Library All Journals |
| subjects | Biprorulus bibax Chemistry Claisen rearrangement Exact sciences and technology Hemiacetals Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones Lipases Organic chemistry Pheromones Preparations and properties |
| title | Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T16%3A07%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Pheromone%20Synthesis,%20CLVIII.%20New%20Synthesis%20and%20Revision%20of%20the%20Absolute%20Configuration%20of%20the%20Hemiacetal%20Pheromone%20of%20the%20Spined%20Citrus%20Bug%20Biprorulus%20bibax&rft.jtitle=Liebigs%20Annalen%20der%20Chemie&rft.au=Mori,%20Kenji&rft.date=1993-12-13&rft.volume=1993&rft.issue=12&rft.spage=1287&rft.epage=1294&rft.pages=1287-1294&rft.issn=0170-2041&rft.eissn=1099-0690&rft.coden=LACHDL&rft_id=info:doi/10.1002/jlac.1993199301210&rft_dat=%3Cistex_cross%3Eark_67375_WNG_55KZTL1G_Q%3C/istex_cross%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 |