Synthetic Efforts Towards Non-Canonical Strigolactones, and Stability Studies of the Bromoallene des-Ethylpanacene.

Abstract

The world is growing at remarkable rate and by 2050, we need solutions to ensure food security for more people. Research shows that we cannot produce enough food to feed a growing population with synthetic pesticides and fertilisers. Strigolactones are a class of photochemical hormones cruical for a plant’s development and survival in stressful environments, and members of the non-canonical strigolactone class are the executive players under the spotlight. The success of our global efforts to end hunger and feed a growing population by 2030 is parallel with knowledge pertaining to understanding how these plant hormones function exactly. This thesis begins with an investigative project, detailing the stability of bromoallenes and the outcomes of my investigations, as well as the enantioselective syntheses of des-ethylpanacene and it’s epimer and the key transformations which allowed for it’s efficient synthesis. Chapter two then begins with an introduction detailing our global commitment to food security, the history of agriculture, the use of pesticides and an introduction to strigolactones, including their biological functions in the plant kingdom, and the previous syntheses published to access strigolactones, in particular the non-canonical class. Chapter three and four detail the Results and Discussion of synthetic efforts towards the total syntheses of two non-canonical strigolactones. Specifically, chapter three details the total synthesis of carlactone (the precursor of all strigolactones), and chapter four details the synthetic efforts explored en route to the asymmetric construction of zealactone a/b. Finally, chapter five details all experimental procedures, and the characterisation of compounds, detailed throughout this thesis.