A protecting group-free synthesis of the Colorado potato beetle pheromone

Zhongtao Wu; Manuel Jäger; Jeffrey Buter; Adriaan Minnaard

A protecting group-free synthesis of the Colorado potato beetle pheromone

Zhongtao Wu, Manuel Jäger, Jeffrey Buter, Adriaan Minnaard

Stratingh Institute, University of Groningen

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

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.

Original language	English
Pages (from-to)	2374-2377
Journal	Beilstein Journal of Organic Chemistry
Volume	9
Publication status	Published - 6 Nov 2013
Externally published	Yes

Keywords

organic chemistry
total synthesis
natural product

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https://doi.org/10.3762/bjoc.9.273Licence: CC BY

Cite this

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title = "A protecting group-free synthesis of the Colorado potato beetle pheromone",

abstract = "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.",

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AB - 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.

KW - organische chemie

KW - totale synthese

KW - natuurlijk product

KW - organic chemistry

KW - total synthesis

KW - natural product

M3 - Article

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SP - 2374

EP - 2377

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

A protecting group-free synthesis of the Colorado potato beetle pheromone

Abstract

Keywords

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