Synthesis of the Four Stereoisomers of 6-Acetoxy-19-methylnonacosane, the Most Potent Component of the Female Sex Pheromone of the New World Screwworm Fly, with Special Emphasis on Partial Racemization in the Course of Catalytic Hydrogenation
Starting from the enantiomers of citronellal and 1-octyn-3-ol, all four stereoisomers of 6-acetoxy-19-methylnonacosane were synthesized with sufficiently high stereochemical purities (more than 90% ee at C-6; about 97% ee at C-19) for their biological testing as the female sex pheromone of the screw...
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| Veröffentlicht in: | European journal of organic chemistry 2004-03, Vol.2004 (5), p.1089-1096 |
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| container_title | European journal of organic chemistry |
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| creator | Mori, K Ohtaki, T Ohrui, H Berkebile, D.R Carlson, D.A |
| description | Starting from the enantiomers of citronellal and 1-octyn-3-ol, all four stereoisomers of 6-acetoxy-19-methylnonacosane were synthesized with sufficiently high stereochemical purities (more than 90% ee at C-6; about 97% ee at C-19) for their biological testing as the female sex pheromone of the screwworm fly (Cochliomyia hominivorax). All four isomers showed strong pheromone activity even at 1 microgram, and no significant difference was observed in their potency. Adams platinum oxide was found to cause partial racemization of enantiomerically pure secondary propargylic alcohols in the course of their catalytic hydrogenation to saturated and secondary alcohols, while palladium-charcoal was less potent in causing partial racemization. A new HPLC-based discrimination of chiral and secondary alcohols proved to be useful in following such a subtle partial racemization. |
| doi_str_mv | 10.1002/ejoc.200300669 |
| format | Article |
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All four isomers showed strong pheromone activity even at 1 microgram, and no significant difference was observed in their potency. Adams platinum oxide was found to cause partial racemization of enantiomerically pure secondary propargylic alcohols in the course of their catalytic hydrogenation to saturated and secondary alcohols, while palladium-charcoal was less potent in causing partial racemization. A new HPLC-based discrimination of chiral and secondary alcohols proved to be useful in following such a subtle partial racemization.</description><identifier>ISSN: 1099-0690</identifier><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200300669</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>6-acetoxy-19-methylnonacosane ; Cochliomyia hominivorax ; hydrocarbons ; Hydrogenation ; insect control ; insect pests ; Liquid chromatography ; myiasis ; Natural products ; Pheromones ; sex pheromones ; stereoisomers ; structure-activity relationships</subject><ispartof>European journal of organic chemistry, 2004-03, Vol.2004 (5), p.1089-1096</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3499-c0372186955f6910cbb94c39f0d76259ef21f69a37fb0d46c8fe1b833491c1903</citedby><cites>FETCH-LOGICAL-c3499-c0372186955f6910cbb94c39f0d76259ef21f69a37fb0d46c8fe1b833491c1903</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200300669$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45554</link.rule.ids></links><search><creatorcontrib>Mori, K</creatorcontrib><creatorcontrib>Ohtaki, T</creatorcontrib><creatorcontrib>Ohrui, H</creatorcontrib><creatorcontrib>Berkebile, D.R</creatorcontrib><creatorcontrib>Carlson, D.A</creatorcontrib><title>Synthesis of the Four Stereoisomers of 6-Acetoxy-19-methylnonacosane, the Most Potent Component of the Female Sex Pheromone of the New World Screwworm Fly, with Special Emphasis on Partial Racemization in the Course of Catalytic Hydrogenation</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Starting from the enantiomers of citronellal and 1-octyn-3-ol, all four stereoisomers of 6-acetoxy-19-methylnonacosane were synthesized with sufficiently high stereochemical purities (more than 90% ee at C-6; about 97% ee at C-19) for their biological testing as the female sex pheromone of the screwworm fly (Cochliomyia hominivorax). All four isomers showed strong pheromone activity even at 1 microgram, and no significant difference was observed in their potency. Adams platinum oxide was found to cause partial racemization of enantiomerically pure secondary propargylic alcohols in the course of their catalytic hydrogenation to saturated and secondary alcohols, while palladium-charcoal was less potent in causing partial racemization. A new HPLC-based discrimination of chiral and secondary alcohols proved to be useful in following such a subtle partial racemization.</description><subject>6-acetoxy-19-methylnonacosane</subject><subject>Cochliomyia hominivorax</subject><subject>hydrocarbons</subject><subject>Hydrogenation</subject><subject>insect control</subject><subject>insect pests</subject><subject>Liquid chromatography</subject><subject>myiasis</subject><subject>Natural products</subject><subject>Pheromones</subject><subject>sex pheromones</subject><subject>stereoisomers</subject><subject>structure-activity relationships</subject><issn>1099-0690</issn><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkVFv0zAUhSMEEmPwyiv-AUu5ThonfpyitmOMrSJMk_Ziue7N4pHElW2Uhp_NL8BN2bQ3nnx0z_mOrnyj6COFGQVIPuOjUbMEIAVgjL-KTihwHgPj8PqFfhu9c-4RADhj9CT6U429b9BpR0xNgiJL88uSyqNFo53p0E4Oi88VerMfY8rjDn0ztr3ppTJO9ng2gd-M82RtPPaelKbbmf6gnlqxky2SCvdk3aA1XXCfvGscyJ2x7ZZUyuIwGNuRZTuekUH7hlQ7VFq2ZNHtGjnt2ZO1tP4w-y4Vdvq39DoMdT-1lWF_N3WX0st29FqRi3FrzQP2U_B99KaWrcMP_97T6Ha5-FFexFc3qy_l-VWs0nn4LAVpntCC8SyrGaegNhs-VymvYZuzJONYJzQYMs3rDWznTBU10k2RBpgqyiE9jWbHXmWNcxZrsbO6k3YUFMThYuJwMfF8sQDwIzDoFsf_pMXi8qZ8ycZHVjuP-2dW2p-C5Wmeibvrlbhf0fJ-zS7F15D_dMzX0gj5YLUTt1UCNNQVkEFapH8BKcS3jw</recordid><startdate>200403</startdate><enddate>200403</enddate><creator>Mori, K</creator><creator>Ohtaki, T</creator><creator>Ohrui, H</creator><creator>Berkebile, D.R</creator><creator>Carlson, D.A</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200403</creationdate><title>Synthesis of the Four Stereoisomers of 6-Acetoxy-19-methylnonacosane, the Most Potent Component of the Female Sex Pheromone of the New World Screwworm Fly, with Special Emphasis on Partial Racemization in the Course of Catalytic Hydrogenation</title><author>Mori, K ; Ohtaki, T ; Ohrui, H ; Berkebile, D.R ; Carlson, D.A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3499-c0372186955f6910cbb94c39f0d76259ef21f69a37fb0d46c8fe1b833491c1903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>6-acetoxy-19-methylnonacosane</topic><topic>Cochliomyia hominivorax</topic><topic>hydrocarbons</topic><topic>Hydrogenation</topic><topic>insect control</topic><topic>insect pests</topic><topic>Liquid chromatography</topic><topic>myiasis</topic><topic>Natural products</topic><topic>Pheromones</topic><topic>sex pheromones</topic><topic>stereoisomers</topic><topic>structure-activity relationships</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mori, K</creatorcontrib><creatorcontrib>Ohtaki, T</creatorcontrib><creatorcontrib>Ohrui, H</creatorcontrib><creatorcontrib>Berkebile, D.R</creatorcontrib><creatorcontrib>Carlson, D.A</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mori, K</au><au>Ohtaki, T</au><au>Ohrui, H</au><au>Berkebile, D.R</au><au>Carlson, D.A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of the Four Stereoisomers of 6-Acetoxy-19-methylnonacosane, the Most Potent Component of the Female Sex Pheromone of the New World Screwworm Fly, with Special Emphasis on Partial Racemization in the Course of Catalytic Hydrogenation</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2004-03</date><risdate>2004</risdate><volume>2004</volume><issue>5</issue><spage>1089</spage><epage>1096</epage><pages>1089-1096</pages><issn>1099-0690</issn><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Starting from the enantiomers of citronellal and 1-octyn-3-ol, all four stereoisomers of 6-acetoxy-19-methylnonacosane were synthesized with sufficiently high stereochemical purities (more than 90% ee at C-6; about 97% ee at C-19) for their biological testing as the female sex pheromone of the screwworm fly (Cochliomyia hominivorax). All four isomers showed strong pheromone activity even at 1 microgram, and no significant difference was observed in their potency. Adams platinum oxide was found to cause partial racemization of enantiomerically pure secondary propargylic alcohols in the course of their catalytic hydrogenation to saturated and secondary alcohols, while palladium-charcoal was less potent in causing partial racemization. A new HPLC-based discrimination of chiral and secondary alcohols proved to be useful in following such a subtle partial racemization.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200300669</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 1099-0690 |
| ispartof | European journal of organic chemistry, 2004-03, Vol.2004 (5), p.1089-1096 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 6-acetoxy-19-methylnonacosane Cochliomyia hominivorax hydrocarbons Hydrogenation insect control insect pests Liquid chromatography myiasis Natural products Pheromones sex pheromones stereoisomers structure-activity relationships |
| title | Synthesis of the Four Stereoisomers of 6-Acetoxy-19-methylnonacosane, the Most Potent Component of the Female Sex Pheromone of the New World Screwworm Fly, with Special Emphasis on Partial Racemization in the Course of Catalytic Hydrogenation |
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