Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

• Adam Drop,
• Hubert Wojtasek and
• Bożena Frąckowiak-Wojtasek

Beilstein J. Org. Chem. 2020, 16, 616–620, doi:10.3762/bjoc.16.57

• particularly interesting example, because it is also a component of the luring mixture used by the bolas spider Mastophora hutchinsoni [3][4]. (6R,7S,2E)-6,7-Epoxy-2-nonenal has been identified as a sex-aggregation pheromone of the red-necked longhorn beetle (Aromia bungii) [5] and its synthesis has been

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

• Zhongtao Wu,
• Manuel Jäger,
• Jeffrey Buter and
• Adriaan J. Minnaard

Beilstein J. Org. Chem. 2013, 9, 2374–2377, doi:10.3762/bjoc.9.273

• Zhongtao Wu Manuel Jager Jeffrey Buter Adriaan J. Minnaard Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands 10.3762/bjoc.9.273 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. Keywords: aggregation pheromone

• insecticides controlling the Colorado potato beetle, and an attractive alternative is to use a pheromone management strategy. An important finding in this connection was the isolation of the male produced aggregation pheromone by Dickens and Oliver et al. in 2002 [7], which was subsequently identified as (S

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

• Robert Hilgraf,
• Nicole Zimmermann,
• Lutz Lehmann,
• Armin Tröger and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141

• defense compounds of ants [25]. More recently, 17 – which shows (R)-configuration at C1 of the side-chain – was found to be a male-produced aggregation pheromone of lacewings [26][27]. The cis-fused iridomyrmecin (1) and dolichodial (18) are constituents of the anal gland secretion of the Argentine ant