Community Research and Development Information Service - CORDIS

Periodic Report Summary 1 - POSIN (Practical Organic Synthesis Inspired by Nature)

Project Objectives:

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 I will investigate and learn about the highly sophisticated way nature utilizes dimerizations to rapidly generate molecular complexity. I will demonstrate the power of this biomimetic strategy by synthesizing a wide variety of complex dimeric natural products including phenylethanoids, alkaloids, lignans, 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. More generally I will learn how nature uses relatively simple processes to rapidly generate molecular complexity in a highly selective manner. In summary the aim of our research is...

1. By mimicking proposed biological processes, devise new synthetic strategies and reactions that will be of broad use in organic synthesis.
2. Improve the science and art of total synthesis by developing short and efficient syntheses of structurally complex natural products.
3. Learn how nature successfully utilizes symmetry to synthesize highly complex molecules that contain no element of symmetry.
4. Provide experimental data that will either support or enable the modification of natural product structures and biosynthetic pathways.
5. Develop a deeper appreciation for the chemistry of life and acquire insight into the origin of natural products and the chemistry of their biosynthetic pathways.

Work Performed Since the Beginning of the Project:

We have made significant progress towards the biomimetic synthesis of several natural products. We have completed the total syntheses of angiopterlactone B and a dimeric thymol derivative (see Main Results Achieved section below). We have made significant progress towards achieving a total synthesis of brosiparin, a key intermediate required to invetsigate our proposed biosynthesis of fatouapilosin.

Main Results Achieved:

We have actually finished the total synthesis of two targets (angiopterlactone B and a dimeric thymol derivative). Each of these syntheses will be published in due course, with one manuscript recently accepted with corrections at Angewandte Chemie and one being prepared. Through the execution of these total syntheses we have provided insight into how nature uses symmetry to synthesize highly complex molecules that contain no element of symmetry. Finally we have been able to revise the structure of one natural product through our synthetic efforts, thus correcting a mistake that was in the literature.

Expected Final Results and Potential Impact:

It is difficult to accurately predict the final results that will be achieved by the end of the project. I certainly expect to finish further total syntheses and to publish these in top international chemistry journals. However, it is difficult to predict the impact these syntheses may have. The biological profiles of these target moelcules will be screened for potentially useful activity, which may lead to spectacular impact. The chemical insights we are acquiring through our synthetic research will have a broad impact on the field of natural product synthesis and natural products chemistry.

Reported by

United Kingdom


Life Sciences
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