Scalable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali
Methyl (E,E,Z)-2,4,6-decatrienoate (1) is the aggregation pheromone of the brown-winged green bug, Plautia stali and is also a pheromone synergist of the brown marmorated stink bug, Halyomorpha halys pheromone. A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate (1) was achie...
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| Veröffentlicht in: | Tetrahedron 2024-05, Vol.158, p.133771, Article 133771 |
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| creator | Ye, Yuangui Zhu, Quan Yuan, Mingquan Huang, Rong Tao, Yunhai |
| description | Methyl (E,E,Z)-2,4,6-decatrienoate (1) is the aggregation pheromone of the brown-winged green bug, Plautia stali and is also a pheromone synergist of the brown marmorated stink bug, Halyomorpha halys pheromone. A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate (1) was achieved in 5 steps. The stereoselective formation of the 4E, 6Z conjugated double bond was accomplished by a tandem addition reaction of acrolein with acetylene and the 2E double bond was formed by a Heck reaction. The pheromone was obtained in 99 % stereochemical purity and 40 % overall yield starting from (Z,E)-7-bromo-4,6-heptadienal.
A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali, was achieved via Heck reaction strategy. [Display omitted] |
| doi_str_mv | 10.1016/j.tet.2023.133771 |
| format | Article |
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A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali, was achieved via Heck reaction strategy. [Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2023.133771</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>acetylene ; acrolein ; aggregation pheromones ; Brown marmorated stink bug ; Brown-winged green bug ; Halyomorpha halys ; Heck reaction ; Pd(II) catalysis ; Pheromone synthesis ; Plautia stali ; stereochemistry ; stereoselectivity</subject><ispartof>Tetrahedron, 2024-05, Vol.158, p.133771, Article 133771</ispartof><rights>2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c282t-396c935af7fda0bfce247c8d1c119cb3e3cd27cd70b7c2652a5840f25e63f4e83</cites><orcidid>0000-0002-1224-4374</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2023.133771$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids></links><search><creatorcontrib>Ye, Yuangui</creatorcontrib><creatorcontrib>Zhu, Quan</creatorcontrib><creatorcontrib>Yuan, Mingquan</creatorcontrib><creatorcontrib>Huang, Rong</creatorcontrib><creatorcontrib>Tao, Yunhai</creatorcontrib><title>Scalable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali</title><title>Tetrahedron</title><description>Methyl (E,E,Z)-2,4,6-decatrienoate (1) is the aggregation pheromone of the brown-winged green bug, Plautia stali and is also a pheromone synergist of the brown marmorated stink bug, Halyomorpha halys pheromone. A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate (1) was achieved in 5 steps. The stereoselective formation of the 4E, 6Z conjugated double bond was accomplished by a tandem addition reaction of acrolein with acetylene and the 2E double bond was formed by a Heck reaction. The pheromone was obtained in 99 % stereochemical purity and 40 % overall yield starting from (Z,E)-7-bromo-4,6-heptadienal.
A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali, was achieved via Heck reaction strategy. [Display omitted]</description><subject>acetylene</subject><subject>acrolein</subject><subject>aggregation pheromones</subject><subject>Brown marmorated stink bug</subject><subject>Brown-winged green bug</subject><subject>Halyomorpha halys</subject><subject>Heck reaction</subject><subject>Pd(II) catalysis</subject><subject>Pheromone synthesis</subject><subject>Plautia stali</subject><subject>stereochemistry</subject><subject>stereoselectivity</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kM1qGzEURkVpIK7TB8hOSxdmXP3O2HRVgtMEAgkk3XQjNHfujGVmJFeSY_wKfeqOcddd3c05H9xDyC1nS8549XW3zJiXggm55FLWNf9AZlxVqtSKVx_JjDHFSsUEuyafUtoxxjgXckb-vIIdbDMgTSeft5hcoqGjI-btaaCLTbEpfn0pRaGKqmwRbI4OfbAZCzrR1PZ9xN5mFzzdbzGGMXikEMb9dH0-T52xJoajL4_O99jSyUBPm0Nf0JfBHrKzNGU7uBty1dkh4ed_d05-3m_e7h7Kp-cfj3ffn0oQK5FLua5gLbXt6q61rOkAhaph1XLgfA2NRAmtqKGtWVODqLSweqVYJzRWslO4knOyuOzuY_h9wJTN6BLgMFiP4ZCM5FrqdaW1mlB-QSGGlCJ2Zh_daOPJcGbO3c3OTN3Nubu5dJ-cbxcHpx_eHUaTYGoG2LqIkE0b3H_sv5qhi-U</recordid><startdate>20240530</startdate><enddate>20240530</enddate><creator>Ye, Yuangui</creator><creator>Zhu, Quan</creator><creator>Yuan, Mingquan</creator><creator>Huang, Rong</creator><creator>Tao, Yunhai</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-1224-4374</orcidid></search><sort><creationdate>20240530</creationdate><title>Scalable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali</title><author>Ye, Yuangui ; Zhu, Quan ; Yuan, Mingquan ; Huang, Rong ; Tao, Yunhai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c282t-396c935af7fda0bfce247c8d1c119cb3e3cd27cd70b7c2652a5840f25e63f4e83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>acetylene</topic><topic>acrolein</topic><topic>aggregation pheromones</topic><topic>Brown marmorated stink bug</topic><topic>Brown-winged green bug</topic><topic>Halyomorpha halys</topic><topic>Heck reaction</topic><topic>Pd(II) catalysis</topic><topic>Pheromone synthesis</topic><topic>Plautia stali</topic><topic>stereochemistry</topic><topic>stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ye, Yuangui</creatorcontrib><creatorcontrib>Zhu, Quan</creatorcontrib><creatorcontrib>Yuan, Mingquan</creatorcontrib><creatorcontrib>Huang, Rong</creatorcontrib><creatorcontrib>Tao, Yunhai</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ye, Yuangui</au><au>Zhu, Quan</au><au>Yuan, Mingquan</au><au>Huang, Rong</au><au>Tao, Yunhai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Scalable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali</atitle><jtitle>Tetrahedron</jtitle><date>2024-05-30</date><risdate>2024</risdate><volume>158</volume><spage>133771</spage><pages>133771-</pages><artnum>133771</artnum><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>Methyl (E,E,Z)-2,4,6-decatrienoate (1) is the aggregation pheromone of the brown-winged green bug, Plautia stali and is also a pheromone synergist of the brown marmorated stink bug, Halyomorpha halys pheromone. A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate (1) was achieved in 5 steps. The stereoselective formation of the 4E, 6Z conjugated double bond was accomplished by a tandem addition reaction of acrolein with acetylene and the 2E double bond was formed by a Heck reaction. The pheromone was obtained in 99 % stereochemical purity and 40 % overall yield starting from (Z,E)-7-bromo-4,6-heptadienal.
A scalable and controllable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali, was achieved via Heck reaction strategy. [Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2023.133771</doi><orcidid>https://orcid.org/0000-0002-1224-4374</orcidid></addata></record> |
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| source | Elsevier ScienceDirect Journals |
| subjects | acetylene acrolein aggregation pheromones Brown marmorated stink bug Brown-winged green bug Halyomorpha halys Heck reaction Pd(II) catalysis Pheromone synthesis Plautia stali stereochemistry stereoselectivity |
| title | Scalable synthesis of methyl (E,E,Z)-2,4,6-decatrienoate, the aggregation pheromone component of the brown-winged green bug, Plautia stali |
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