Loading…

Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri

The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidat...

Full description

Saved in:

Bibliographic Details
Published in:	Journal of agricultural and food chemistry 2004-05, Vol.52 (10), p.2896-2899
Main Authors:	Passaro, Linda C, Webster, Francis X
Format:	Article
Language:	English
Subjects:	Animals Biological and medical sciences Biological control Citrus Control females Fundamental and applied biological sciences. Psychology Hemiptera - chemistry insect pests Magnetic Resonance Spectroscopy Phytopathology. Animal pests. Plant and forest protection Planococcus citri Protozoa. Invertebrates Sex Attractants - chemical synthesis sex pheromones synthesis
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-a434t-2cc68fbf074f154be6e29b5ccebff5a07460bf558dd174404d90e43654408eb33
cites	cdi_FETCH-LOGICAL-a434t-2cc68fbf074f154be6e29b5ccebff5a07460bf558dd174404d90e43654408eb33
container_end_page	2899
container_issue	10
container_start_page	2896
container_title	Journal of agricultural and food chemistry
container_volume	52
creator	Passaro, Linda C Webster, Francis X
description	The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3−NaIO4, and methylenation with Zn/CH2Br2/TiCl4. Keywords: (+)-cis-Planococcyl acetate; synthesis; pheromones; olefination; oxidation
doi_str_mv	10.1021/jf035301h
format	article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71919849</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71919849</sourcerecordid><originalsourceid>FETCH-LOGICAL-a434t-2cc68fbf074f154be6e29b5ccebff5a07460bf558dd174404d90e43654408eb33</originalsourceid><addsrcrecordid>eNqF0U1v1DAQBmALgehSOPAHIBeQkAjMxHbsHNGKUlA_Vtr2bDnecTdLsm7tROr-e4x2aTkgcfLI76OxPWbsNcInhAo_bzxwyQHXT9gMZQWlRNRP2QxyWGpZ4xF7kdIGALRU8JwdoUSuNK9m7HK5245rSl0qgi9yVZzQYHsqlnRfLNYUwxC29Cebd2OcUnFOtt-1083HYtHbbXDBubzrcti9ZM-87RO9OqzH7Prk69X8tDy7_PZ9_uWstIKLsaycq7VvPSjhUYqWaqqaVjpHrffS5u0aWi-lXq1QCQFi1QAJXstca2o5P2bv931vY7ibKI1m6JKjPt-HwpSMwgYbLZr_QlRaCeAqww976GJIKZI3t7EbbNwZBPN7zOZhzNm-OTSd2oFWj_Iw1wzeHYBNzvY-2q3r0l9OcV2Bzq7cuy6NdP-Q2_jT1Ioraa4WSyN-nJ7jBVfmIvu3e-9tMPYm5p7XywqQAzQCGtU8nmxdMpswxW3-hn884ReqdaeJ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>17874037</pqid></control><display><type>article</type><title>Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Passaro, Linda C ; Webster, Francis X</creator><creatorcontrib>Passaro, Linda C ; Webster, Francis X</creatorcontrib><description>The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3−NaIO4, and methylenation with Zn/CH2Br2/TiCl4. Keywords: (+)-cis-Planococcyl acetate; synthesis; pheromones; olefination; oxidation</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf035301h</identifier><identifier>PMID: 15137832</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Biological and medical sciences ; Biological control ; Citrus ; Control ; females ; Fundamental and applied biological sciences. Psychology ; Hemiptera - chemistry ; insect pests ; Magnetic Resonance Spectroscopy ; Phytopathology. Animal pests. Plant and forest protection ; Planococcus citri ; Protozoa. Invertebrates ; Sex Attractants - chemical synthesis ; sex pheromones ; synthesis</subject><ispartof>Journal of agricultural and food chemistry, 2004-05, Vol.52 (10), p.2896-2899</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a434t-2cc68fbf074f154be6e29b5ccebff5a07460bf558dd174404d90e43654408eb33</citedby><cites>FETCH-LOGICAL-a434t-2cc68fbf074f154be6e29b5ccebff5a07460bf558dd174404d90e43654408eb33</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&idt=15738208$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15137832$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Passaro, Linda C</creatorcontrib><creatorcontrib>Webster, Francis X</creatorcontrib><title>Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3−NaIO4, and methylenation with Zn/CH2Br2/TiCl4. Keywords: (+)-cis-Planococcyl acetate; synthesis; pheromones; olefination; oxidation</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Biological control</subject><subject>Citrus</subject><subject>Control</subject><subject>females</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hemiptera - chemistry</subject><subject>insect pests</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Planococcus citri</subject><subject>Protozoa. Invertebrates</subject><subject>Sex Attractants - chemical synthesis</subject><subject>sex pheromones</subject><subject>synthesis</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqF0U1v1DAQBmALgehSOPAHIBeQkAjMxHbsHNGKUlA_Vtr2bDnecTdLsm7tROr-e4x2aTkgcfLI76OxPWbsNcInhAo_bzxwyQHXT9gMZQWlRNRP2QxyWGpZ4xF7kdIGALRU8JwdoUSuNK9m7HK5245rSl0qgi9yVZzQYHsqlnRfLNYUwxC29Cebd2OcUnFOtt-1083HYtHbbXDBubzrcti9ZM-87RO9OqzH7Prk69X8tDy7_PZ9_uWstIKLsaycq7VvPSjhUYqWaqqaVjpHrffS5u0aWi-lXq1QCQFi1QAJXstca2o5P2bv931vY7ibKI1m6JKjPt-HwpSMwgYbLZr_QlRaCeAqww976GJIKZI3t7EbbNwZBPN7zOZhzNm-OTSd2oFWj_Iw1wzeHYBNzvY-2q3r0l9OcV2Bzq7cuy6NdP-Q2_jT1Ioraa4WSyN-nJ7jBVfmIvu3e-9tMPYm5p7XywqQAzQCGtU8nmxdMpswxW3-hn884ReqdaeJ</recordid><startdate>20040519</startdate><enddate>20040519</enddate><creator>Passaro, Linda C</creator><creator>Webster, Francis X</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QR</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20040519</creationdate><title>Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri</title><author>Passaro, Linda C ; Webster, Francis X</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a434t-2cc68fbf074f154be6e29b5ccebff5a07460bf558dd174404d90e43654408eb33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Biological control</topic><topic>Citrus</topic><topic>Control</topic><topic>females</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hemiptera - chemistry</topic><topic>insect pests</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Planococcus citri</topic><topic>Protozoa. Invertebrates</topic><topic>Sex Attractants - chemical synthesis</topic><topic>sex pheromones</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Passaro, Linda C</creatorcontrib><creatorcontrib>Webster, Francis X</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Chemoreception Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Passaro, Linda C</au><au>Webster, Francis X</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2004-05-19</date><risdate>2004</risdate><volume>52</volume><issue>10</issue><spage>2896</spage><epage>2899</epage><pages>2896-2899</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3−NaIO4, and methylenation with Zn/CH2Br2/TiCl4. Keywords: (+)-cis-Planococcyl acetate; synthesis; pheromones; olefination; oxidation</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15137832</pmid><doi>10.1021/jf035301h</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0021-8561
ispartof	Journal of agricultural and food chemistry, 2004-05, Vol.52 (10), p.2896-2899
issn	0021-8561 1520-5118
language	eng
recordid	cdi_proquest_miscellaneous_71919849
source	American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects	Animals Biological and medical sciences Biological control Citrus Control females Fundamental and applied biological sciences. Psychology Hemiptera - chemistry insect pests Magnetic Resonance Spectroscopy Phytopathology. Animal pests. Plant and forest protection Planococcus citri Protozoa. Invertebrates Sex Attractants - chemical synthesis sex pheromones synthesis
title	Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri
url	http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T09%3A42%3A07IST&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=Synthesis%20of%20the%20Female%20Sex%20Pheromone%20of%20the%20Citrus%20Mealybug,%20Planococcus%20citri&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Passaro,%20Linda%20C&rft.date=2004-05-19&rft.volume=52&rft.issue=10&rft.spage=2896&rft.epage=2899&rft.pages=2896-2899&rft.issn=0021-8561&rft.eissn=1520-5118&rft.coden=JAFCAU&rft_id=info:doi/10.1021/jf035301h&rft_dat=%3Cproquest_cross%3E71919849%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a434t-2cc68fbf074f154be6e29b5ccebff5a07460bf558dd174404d90e43654408eb33%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=17874037&rft_id=info:pmid/15137832&rfr_iscdi=true