A new enantioselective synthesis of the four stereoisomers of pallantione, the male-produced sex pheromone of Pallantia macunaima (Heteroptera: Pentatomidae). Issue 1 (4th January 2018)

• Record Type: Journal Article
• Authors: Soldi, Rafael Augusto; Szczerbowski, Daiane; Zarbin, Paulo Henrique Gorgatti
• Is Part Of: Tetrahedron. Volume 74:Issue 1(2018)
• Page Start: 88
• Page End: 95
• Publication Date: 2018-01-04
• Subjects: 6, 10, 13-Trimethyltetradecan-2-one -- Pallantia macunaima -- Sex pheromone -- Semiochemicals -- Pentatomidae; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.11.043
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: In a previous study we reported the identification of the first ketone found in the Pentatomidae family, the sex attractant pheromone of the male stink bug Pallantia macunaima, (6 R, 10 S )-6, 10, 13-trimethyltetradecan-2-one. Here we describe an efficient enantioselective route for the synthesis of the four stereoisomers of this pheromone. The synthesis was conceived as the connection of two chiral building blocks, employing ( R )- or ( S )-citronellol and methyl ( S )-3-hydroxy-2-methylpropionate as the source of chirality. Graphical abstract: