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Synthesis of Lamellarin alkaloids using a photoredox initiated cyclisation cascade


   Department of Chemistry


About the Project

Loughborough University has seen 94% of our research impact rated as ‘world-leading’ or ‘internationally excellent’, underlining the wide-ranging positive impacts that our research has on the world (REF, 2021).

In choosing Loughborough for your research, you’ll work alongside academics who are leaders in their field. You will benefit from comprehensive support and guidance from our Doctoral College, including tailored careers advice, to help you succeed in your research and future career. Find out more.

Reference code: CM/MK-Un2/2021

Campus: Loughborough

Start date: January 2022, April 2022, July 2022, October 2022

Full-time/part-time availability: Full-time (3 years)

Fee band (2021/22 academic year): Band RB (UK: £4,500; international: £24,100)

Link to supervisor's online staff profile page: https://www.lboro.ac.uk/departments/chemistry/staff/academic-research/marc-kimber/

Link to supervisor's online staff profile page: https://www.lboro.ac.uk/departments/chemistry/staff/academic-research/gareth-pritchard/

Project detail:

More than 70 lamellarins and related pyrrole-derived alkaloids have been isolated and identified [1]. While they posses a variety of unique structural features they also exhibit fascinating and significant biological properties. These include cytotoxicity and antitumor activity, multidrug resistance (MDR), HIV-1 integrase inhibition, antibiotic activity, cell division inhibition, immuno-modulatory activity, antioxidant activity, and feeding deterrence.[ref] Traditional syntheses of this natural product class compounds have centered on palladium coupling of pyrrole bromides with aryl boronic acids with subsequent alkylation of the pyrrole nitrogen or Diels-Alder reaction of a disubstituted alkynes with subsequent functional group manipulation. Our approach will utilize our recently reported photoredox mediated addition of radicals to enamides,[2] followed by subsequent nucleophile trapping. This project will develop an intramolecular variant of this unique process that will ultimately deliver a total synthesis of the core heterocyclic structure of the lamellarins. This project will significantly increase the synthetic efficiency compared to current strategies, as well as providing an excellent training platform to the prospective PhD candidate in our new state-of-the-art laboratories here at Loughborough.

Entry requirements:

2:1 honours degree (or equivalent international qualification) in a relevant subject.

English language requirements: Applicants must meet the minimum English language requirements. Further details are available on the international website: http://www.lboro.ac.uk/international/applicants/english/

How to apply:

All applications should be made online: https://www.lboro.ac.uk/study/postgraduate/apply/research-applications/

Under school/department name, select ‘Chemistry’. Please quote reference CM/MK-Un2/2021.

The deadline for applications is 30th September 2022.


References

[1] Fan, H. et al. Chem Rev. 2008, 108, 264; [2] Kimber, M. C. et al. Beil. J. Org. Chem. 2020, 16, 1983; Kimber, M. C. et al. Org. Lett. 2018, 20, 1003.

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