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New Discoveries in Organic Synthesis Inspired by the Efficiency of Nature. Nature can assemble complex organic molecules from simple starting materials with apparent ease, but the laboratory synthesis of these natural products is very difficult. This project aims to mimic the way in which Nature constructs organic compounds and thus develop more efficient, greener synthetic processes in which there is a rapid build up of molecular complexity via “biomimetic” reactions. We will integrate this app ....New Discoveries in Organic Synthesis Inspired by the Efficiency of Nature. Nature can assemble complex organic molecules from simple starting materials with apparent ease, but the laboratory synthesis of these natural products is very difficult. This project aims to mimic the way in which Nature constructs organic compounds and thus develop more efficient, greener synthetic processes in which there is a rapid build up of molecular complexity via “biomimetic” reactions. We will integrate this approach with modern methods of catalysis, including electrochemistry, photochemistry and biocatalysis. As a result, this work will expand the chemical space available to synthetic chemists working in the pharmaceutical industry. A further benefit is the training of the next generation of Australian synthetic chemists. Read moreRead less
Biomimetic Synthesis of Dimeric Natural Products. The aim of this research is to use nature as a source of inspiration and direction to improve and develop synthetic organic chemistry. Through targeted total syntheses this project will investigate and learn about the highly sophisticated way nature utilises dimerizations to rapidly generate molecular complexity. This project will demonstrate the power of this biomimetic strategy by synthesising a wide variety of complex dimeric natural products ....Biomimetic Synthesis of Dimeric Natural Products. The aim of this research is to use nature as a source of inspiration and direction to improve and develop synthetic organic chemistry. Through targeted total syntheses this project will investigate and learn about the highly sophisticated way nature utilises dimerizations to rapidly generate molecular complexity. This project will demonstrate the power of this biomimetic strategy by synthesising a wide variety of complex dimeric natural products including phenylethanoids, alkaloids, lignans, terpenes and coumarins. The expected outcome will be uniquely efficient synthetic strategies that significantly surpass all previous approaches and new synthetic methodology that will be of broad use in organic synthesis.Read moreRead less
Using natural products to inspire discoveries in synthesis and biosynthesis. This project aims to understand the organic chemistry that occurs in the biosynthesis of unusual antibiotic natural products by marine microorganisms. In an interdisciplinary approach, proposed biosynthetic intermediates will be synthesised and screened against newly isolated enzymes from the microorganisms of interest. This will allow the elucidation of biosynthetic pathways, and aid the discovery of new chemoenzymatic ....Using natural products to inspire discoveries in synthesis and biosynthesis. This project aims to understand the organic chemistry that occurs in the biosynthesis of unusual antibiotic natural products by marine microorganisms. In an interdisciplinary approach, proposed biosynthetic intermediates will be synthesised and screened against newly isolated enzymes from the microorganisms of interest. This will allow the elucidation of biosynthetic pathways, and aid the discovery of new chemoenzymatic reactivity that may be broadly useful in organic synthesis. Non-enzymatic, predisposed organic reactions will also be uncovered during the project. The benefit of this project will be an improvement in our ability to synthesise potential antibiotics using a combined synthetic organic and chemoenzymatic approach. This could lead to useful new antibiotics in the future.Read moreRead less
Polarity inversion of conjugate acceptors: New opportunities in catalysis. Conjugate acceptors are common chemicals that are readily available from petrochemical and biomass feedstocks. While they are used extensively to build functional materials, including polymers and medicines, the reactions that they can engage in are largely limited to those exploiting their natural reactivity. In this project, catalysis will be used to allow these ubiquitous building blocks to react in entirely new ways. ....Polarity inversion of conjugate acceptors: New opportunities in catalysis. Conjugate acceptors are common chemicals that are readily available from petrochemical and biomass feedstocks. While they are used extensively to build functional materials, including polymers and medicines, the reactions that they can engage in are largely limited to those exploiting their natural reactivity. In this project, catalysis will be used to allow these ubiquitous building blocks to react in entirely new ways. In doing so new chemical reactions will be discovered that convert simple building blocks into sophisticated fine chemicals. The potential utility of the products is diverse and will enable future applications in fields focused on the preparation of functional materials. Read moreRead less
Extending the frontiers of organocatalysis: new reactions involving nucleophilic carbenes. High technology solutions to the problems of today and tomorrow require new materials designed for specific activities. This project will deliver new technologies for the rapid and efficient assembly of materials designed for function.
Challenges to organocatalysis. This project aims to use organocatalysis to generate organocatalytic C=C insertion, C-H functionalisation and carbonyl ylide/1,3-dipolar cycloaddition reactions. Organocatalysis has transformed the way chemical synthesis is performed. However, in the early years the focus of this discipline has primarily been enolate type chemistry, and more challenging reactions, such as those involving carbenoid intermediates, have not been contemplated. Previously such reactions ....Challenges to organocatalysis. This project aims to use organocatalysis to generate organocatalytic C=C insertion, C-H functionalisation and carbonyl ylide/1,3-dipolar cycloaddition reactions. Organocatalysis has transformed the way chemical synthesis is performed. However, in the early years the focus of this discipline has primarily been enolate type chemistry, and more challenging reactions, such as those involving carbenoid intermediates, have not been contemplated. Previously such reactions have only been achieved using transition metal catalysts. This project addresses this limitation, allowing the strengths of organocatalysis (abundance and diversity, access to enantiopurity, elemental sustainability) to affect the broader landscape of catalysis. This approach could present an opportunity to examine reactivity patterns, stereoselectivity and cascade design and may lead to new reaction technologies.Read moreRead less
Lessons From Nature: Late Stage Oxidation in Total Synthesis. This project aims to achieve the chemical synthesis of a number of biologically active novel natural products. The key aspect is the application of chemistry inspired by Nature to deliver molecular complexity in a rapid fashion which would allow for the production of molecules otherwise unavailable in sufficient quantities from the natural sources. This research will utilize late stage oxidation of intermediates to provide ready acces ....Lessons From Nature: Late Stage Oxidation in Total Synthesis. This project aims to achieve the chemical synthesis of a number of biologically active novel natural products. The key aspect is the application of chemistry inspired by Nature to deliver molecular complexity in a rapid fashion which would allow for the production of molecules otherwise unavailable in sufficient quantities from the natural sources. This research will utilize late stage oxidation of intermediates to provide ready access to complex molecules. The main goal is the development of new chemical and biological catalysts for further application in organic synthesis with a view to the production of new medicinal agents and important materials.Read moreRead less
New Reaction Cascades Exploiting N-Heterocyclic Carbenes. Catalytic reactions can enhance the efficiency of chemical synthesis, decreasing environmental and financial cost. This project will undertake the discovery and development of reactions in which a catalyst enables a "production line" of events to provide complex and valuable products. These reactions will proceed with high shape selectivity (enantioselectivity). In addition to new chemical transformations the output of these studies inclu ....New Reaction Cascades Exploiting N-Heterocyclic Carbenes. Catalytic reactions can enhance the efficiency of chemical synthesis, decreasing environmental and financial cost. This project will undertake the discovery and development of reactions in which a catalyst enables a "production line" of events to provide complex and valuable products. These reactions will proceed with high shape selectivity (enantioselectivity). In addition to new chemical transformations the output of these studies includes intellectual capital and human resources, all of which are integral to sustaining a strong chemical manufacturing sector.Read moreRead less
Ring-Strain Relief: Applications in Total Synthesis. This proposal aims to investigate the chemical synthesis of a number of structurally different natural product target molecules by strategies involving the use of either three or four membered ring-strained compounds to afford key synthetic intermediates in an efficient manner. The key aim of this research is to provide more efficient routes to complex natural products and analogues. The research strives to be at the forefront of modern synthe ....Ring-Strain Relief: Applications in Total Synthesis. This proposal aims to investigate the chemical synthesis of a number of structurally different natural product target molecules by strategies involving the use of either three or four membered ring-strained compounds to afford key synthetic intermediates in an efficient manner. The key aim of this research is to provide more efficient routes to complex natural products and analogues. The research strives to be at the forefront of modern synthetic organic chemistry and aims to contribute to the Science of complex molecule synthesis.Read moreRead less
Discovery Early Career Researcher Award - Grant ID: DE130100689
Funder
Australian Research Council
Funding Amount
$375,000.00
Summary
Applying nature's chemistry to the synthesis of complex bioactive natural products. Organic molecules come in all shapes and sizes, and the synthesis of them is crucial to industries as diverse as pharmaceuticals, electronics, cosmetics and agrochemicals. This project aims to develop new ways of making unusual and potentially useful naturally occurring organic molecules using chemistry that mimics how they are formed in nature.