Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

• Eric Gayon,
• Guillaume Lefèvre,
• Olivier Guerret,
• Adrien Tintar and
• Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

• insect sex pheromones as an alternative to conventional pesticides is in constant growth. In this report, we discuss the recent contributions brought by our groups in the field of iron-catalyzed cross-couplings applied to the synthesis of insect pheromones. The pivotal question of the development of

• sustainable synthetic procedures involving cheap, non-toxic and efficient additives is also discussed, as well as the mechanistic features guiding the reactivity of such catalytic systems. Keywords: catalysis; cross-coupling; insect pheromones; iron; Introduction Public health issues related to

• mechanisms to help regulate/balance the populations of harmful species rather than eradicating them) based on the use of insect pheromones [2][3][4][5] is an eco-friendly solution for the protection of a wide range of crops and plants against pests. Indeed, those chemical mediators, which are emitted by

Aqueous olefin metathesis: recent developments and applications

• Valerio Sabatino and
• Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

• applications of olefin metathesis in chemical biology were reported with “ill-defined” catalysts such as RuCl3·H2O to synthesize insect pheromones by olefin metathesis [77][78]. The development of well-defined ruthenium-based catalysts increased the number of olefin metathesis applications in chemical biology

Identification, synthesis and mass spectrometry of a macrolide from the African reed frog Hyperolius cinnamomeoventris

• Markus Menke,
• Pardha Saradhi Peram,
• Iris Starnberger,
• Walter Hödl,
• Gregory F.M. Jongsma,
• David C. Blackburn,
• Mark-Oliver Rödel,
• Miguel Vences and
• Stefan Schulz

Beilstein J. Org. Chem. 2016, 12, 2731–2738, doi:10.3762/bjoc.12.269

• reed frog, Hyperolius cinnamomeoventris. The location and configuration of the double bond might be relevant for their function, as it is the case in many insect pheromones. In typical pheromone components of insects, including long chain alkenes, alkenols, or unsaturated aldehydes, the location of the

Toward an integrated route to the vernonia allenes and related sesquiterpenoids

• Da Xu,
• Michael A. Drahl and
• Lawrence J. Williams

Beilstein J. Org. Chem. 2011, 7, 937–943, doi:10.3762/bjoc.7.104

• terrestrial plants, algae, and insect pheromones that purportedly have anticancer, antifungal, and antibiotic activity, among others. For example, parthenolide (6) has anti-inflammatory and anti-hyperalgesic effects and induces apoptosis of human acute myelogenous leukemia stem and progenitor cells [24