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](2)OTf(2). Employing this approach, the p...

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Detalles Bibliográficos
Autores principales: Wu, Zhongtao, Jäger, Manuel, Buter, Jeffrey, Minnaard, Adriaan J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869274/
https://www.ncbi.nlm.nih.gov/pubmed/24367402
http://dx.doi.org/10.3762/bjoc.9.273
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author Wu, Zhongtao
Jäger, Manuel
Buter, Jeffrey
Minnaard, Adriaan J
author_facet Wu, Zhongtao
Jäger, Manuel
Buter, Jeffrey
Minnaard, Adriaan J
author_sort Wu, Zhongtao
collection PubMed
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](2)OTf(2). Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol.
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spelling pubmed-38692742013-12-23 A protecting group-free synthesis of the Colorado potato beetle pheromone Wu, Zhongtao Jäger, Manuel Buter, Jeffrey Minnaard, Adriaan J Beilstein J Org Chem Letter 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](2)OTf(2). Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol. Beilstein-Institut 2013-11-06 /pmc/articles/PMC3869274/ /pubmed/24367402 http://dx.doi.org/10.3762/bjoc.9.273 Text en Copyright © 2013, Wu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Wu, Zhongtao
Jäger, Manuel
Buter, Jeffrey
Minnaard, Adriaan J
A protecting group-free synthesis of the Colorado potato beetle pheromone
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 Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869274/
https://www.ncbi.nlm.nih.gov/pubmed/24367402
http://dx.doi.org/10.3762/bjoc.9.273
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