Pheromone synthesis. Part 264: Synthesis of the core 3-oxabicyclo [3.3.0]octane structures of gomadalactones A, B and C, the components of the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca

摘要

The core bicyclic cyclopentanelactone structures of gomadalactones A, B and C with alpha-hydroxyketone system were synthesized from (R)-pulegone, employing deconjugation of an alpha,beta-unsaturated lactone as the key step. Comparison of the CD spectra of the synthetic compounds with those of the natural products confirmed the absolute configuration of the natural pheromone components as proposed in 2007. X-ray crystallographic analysis of the model compound of gomadalactone B core structure was carried out. (C) 2019 Elsevier Ltd. All rights reserved.