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A protecting group-free synthesis of the Colorado potato beetle pheromone.
Wu, Zhongtao; Jäger, Manuel; Buter, Jeffrey; Minnaard, Adriaan J.
Affiliation
  • Wu Z; Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
  • Jäger M; Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
  • Buter J; Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
  • Minnaard AJ; Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
Beilstein J Org Chem ; 9: 2374-7, 2013.
Article in En | MEDLINE | ID: mdl-24367402
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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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Beilstein J Org Chem Year: 2013 Document type: Article Affiliation country: Netherlands
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Beilstein J Org Chem Year: 2013 Document type: Article Affiliation country: Netherlands