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Synthesis of Lamellarin alkaloids using a photoredox initiated cyclisation cascade


   Department of Chemistry


Loughborough United Kingdom Synthetic Chemistry

About the Project

Reference code: CM/MK-Un2/2021

Campus: Loughborough

Start date: January 2021, April 2021, July 2021, October 2021

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

Fee band: Band RB (UK/EU: TBC; international: £22,350)

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 2021.


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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