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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.

SUBMITTER: Wu Z

PROVIDER: S-EPMC3869274 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Wu Zhongtao Z Jäger Manuel M Buter Jeffrey J Minnaard Adriaan J AJ

Beilstein journal of organic chemistry 20131106

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. ...[more]

PMID: 24367402

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