Synthesis of strigolactone and karrikin analogues by gold mediated cyclisation

Karrikins (KARs) and strigolactones (SLs) are two classes of molecules which have a large impact on plant growth and development. KARs are spontaneously formed from burning plant material. Seeds use them as a germination signal to take advantage of reduced competition after bushfires. SLs also induce germination but have a much broader role, serving as true phytohormones. At first glance KARs and SLs look quite different at the molecular level, but they share common structural features as well as common signaling responses, originating from their evolutionary history.
This project will take advantage of recent developments in alkyne cyclisation and gold catalysis to synthesize chemicals closely resembling KARs and SLs, in an economic and efficient way.
A first objective is to develop fluorescent SL analogues, allowing easy detection of the compounds
during research. How exactly SLs elicit a response is still largely unknown. The preparation of compounds that are visible under a microscope will be a large aid to track the destiny of the molecules in cells and unravel their biological mode of action.
A second objective is to slightly modify the common structural part of both plant growth
regulators. Thus, it will be possible to misguide the plant enzymatic system. Using this approach, we will obtain compounds which show an increase in bioactivity or block bioactivity completely.
Both cases are highly wanted by the agrochemical industry.