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A General Strategy for the Iterative Assembly of Complex 1,3-Polyol Motifs

Periodic Reporting for period 1 - GRITAP (A General Strategy for the Iterative Assembly of Complex 1,3-Polyol Motifs)

Reporting period: 2017-07-01 to 2019-06-30

We achieve the development of an iterative chain growth strategy for the synthesis of any 1,3-polyol motif with tailored shapes. The proposed method will allow complete control over the relative and absolute stereochemistry of both non-symmetric and C2-symmetric 1,3-polyols. The power of this methodology will be exemplified through its application to the synthesis of the highly complex polyacetate natural product, bahamaolide A for the first time in less than 15 steps from a cheap commodity 1,4-pentadiene (a protecting-group-free approach).

This project seeks to develop new shorter routes to synthesize medicinally important natural products and their analogues, a reduction in the number of steps will not only reduce the cost, but also make larger scale production feasible. We also expect to have the opportunity to participate in early process to identify molecules which possess suitable characteristics to make potential drug through the cooperation with other scientific groups in the future. Therefore, the fellowship will have a direct impact on EU society and economy not only because it will facilitate the synthesis of complex structural motifs (leading to less waste- economic) but also because the generation of new drug-like molecules has the potential to benefit the population (societal).
In the next sections, an overview of the objectives, the work carried out and details of the dissemination of the action are presented. The project has mostly achieved its objectives and milestones proposed in the original DoA and some minor modifications of the original plan were found to be necessary. The fields of Iterative Assembly of Complex 1,3-Poly Functional Molecules have been created thanks to this Action, and the following project milestones were correctly achieved (better details in the following sections):
1. Development of a general strategy towards the one-directional synthesis of poly-boronic esters and completing the scope herein.
2. Development of a general strategy towards the two-directional synthesis of poly-boronic esters and completing the scope herein
3. Completing the scope of poly-transformation of poly-boronic esters.
4. Completing the product derivatization of poly-functional molecules.
5. Completing the scope of octa-boronic ester synthesis and its application.
6. Towards the synthesis of bahamaolide A.

Overall, the project has introduced a very exciting new area in boron chemistry, which is now enabling the synthesis of poly-functional molecules and hydroxyl-rich natural products from simple boron atom.
Impact
Most the tasks detailed in the DoA have been successfully achieved, except for minor modifications. The plan for dissemination has also been followed with just minor modifications. The description of the impact detailed in the original DoA is, therefore, still relevant for this project.
Overall, the general impact could be described as following.
Impact on the researcher's career. The Fellow has gained a lot of experiences during the implementation of this project. He has also established his research network with many outstanding young chemists in the host group and has established his reputation in the field of boron chemistry presenting his work in international conferences. As a result, the Fellow obtained an independent research academic position in a prestigious university in Taiwan.
Contributing to European Research Area and EU priorities. Harnessing chemical technologies effectively and sustainably is a key element for achieving EU sustainable development. This project introduces an efficient methodology toward complex natural product synthesis. This will contribute to ensure a EU sustainable future.
Impact on the academic community. The chemistry detailed in this action has tremendously impacted academia, triggering growing interest about the topics discovered.
Impact on the industry. Boronic esters are highly useful motifs in organic synthesis, the chemistry discovered during this project opened new significant chemical space. The discoveries are expected to significantly impact the chemical and the pharmaceutical industry introducing new avenues to synthesise previously inaccessible compounds. And the natural product produced in this project has the potential for further pharmaceutical reagent development.
The Fellow has followed the plan detailed on the DoA, with some minor modifications, detailed as following.
1. The Fellow has written and published an outreach/education article sponsored by the University of Bristol ChemLabs. The purpose of this article is to motivate general public to get inspiration from the science. The article can be found in the following picture.
2. As reported in the original DoA the Fellow planned to take part in the Bristol Bright Night, an event organised by the University of Bristol in order to allow researchers to expose the general public to the research ongoing within the University. Unfortunately, in 2017 this event did not take place. However, with the help of the Bristol ChemLab Staff, the Fellow has contributed to organise the Bristol Marie Skłodowska-Curie Open Day, where all the Fellows from university had the opportunity to showcase their research to the general public. The result has been a fantastic day of science and discussion with young students and families. We also take advantage of this opportunity to create one poster to introduce all Marie Skłodowska-Curie Fellow who work at University of Bristol, the picture can be found below.
3. In the DoA the Fellow proposed the attendance of one conference: the 256th ACS National Meeting & Exposition (Boston (MA), USA, 19th-23rd August 2018). Due to better speaker outline and other practical reasons, the Fellow attended, instead, the following two renown conferences: 16th BOSS Meeting (Belgium, July, 2018) and Tetrahedron Symposium, Bangkok, 2019 (delivering a poster presentation). In the dissemination activities the European Union has been acknowledged following the rules detailed in the EU Horizon-2020 portal.
4. In addition to the activities detailed in the DoA, the Fellow has organised a dissemination tour in Asian universities (Taiwan and Thailand). The work detailed in this project has been presented to an audience of BSc, MSc and PhD students and academics. Seminars has been organised in the National Tsing-Hua University (Taiwan), National Sun Yat-sen University (Taiwan) and Mahidol University (Thailand). Details about the oral presentation held in National Tsing-Hua University (Taiwan) can be found at the addr
outreach/education article
Scheme 1. Objective of the whole project
Bristol Marie Skłodowska-Curie Open Day poster