A protecting group-free synthesis of the Colorado potato beetle pheromone
A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]2OTf2. Employing this approach, the phero...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.273 |
| _version_ | 1830192477825400832 |
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| author | Zhongtao Wu Manuel Jäger Jeffrey Buter Adriaan J. Minnaard |
| author_facet | Zhongtao Wu Manuel Jäger Jeffrey Buter Adriaan J. Minnaard |
| author_sort | Zhongtao Wu |
| collection | DOAJ |
| description | A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]2OTf2. Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol. |
| first_indexed | 2024-12-17T23:57:11Z |
| format | Article |
| id | doaj.art-e9b98462b29d4385b0027800935e331b |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T23:57:11Z |
| publishDate | 2013-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e9b98462b29d4385b0027800935e331b2022-12-21T21:28:02ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-11-01912374237710.3762/bjoc.9.2731860-5397-9-273A protecting group-free synthesis of the Colorado potato beetle pheromoneZhongtao Wu0Manuel Jäger1Jeffrey Buter2Adriaan J. Minnaard3Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The NetherlandsStratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The NetherlandsStratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The NetherlandsStratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The NetherlandsA novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]2OTf2. Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol.https://doi.org/10.3762/bjoc.9.273aggregation pheromonecatalysisColorado potato beetleLeptinotarsa decemlineataoxidationnatural product |
| spellingShingle | Zhongtao Wu Manuel Jäger Jeffrey Buter Adriaan J. Minnaard A protecting group-free synthesis of the Colorado potato beetle pheromone Beilstein Journal of Organic Chemistry aggregation pheromone catalysis Colorado potato beetle Leptinotarsa decemlineata oxidation natural product |
| title | A protecting group-free synthesis of the Colorado potato beetle pheromone |
| title_full | A protecting group-free synthesis of the Colorado potato beetle pheromone |
| title_fullStr | A protecting group-free synthesis of the Colorado potato beetle pheromone |
| title_full_unstemmed | A protecting group-free synthesis of the Colorado potato beetle pheromone |
| title_short | A protecting group-free synthesis of the Colorado potato beetle pheromone |
| title_sort | protecting group free synthesis of the colorado potato beetle pheromone |
| topic | aggregation pheromone catalysis Colorado potato beetle Leptinotarsa decemlineata oxidation natural product |
| url | https://doi.org/10.3762/bjoc.9.273 |
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