Natural product chemistry has been a main theme of research at the Oxford Organic Chemistry Department. My research interests are focused on the synthesis of biologically active natural products, with a taste in biomimetic chemistry, and the development of new synthetic methodologies. The biomimetic synthesis of natural products can be very simple and elegant. Nature has perfected the biosynthesis of natural products through millions of years of evolution. These biological transformations have inspired organic chemists to design natural product synthesis, using strategies and chemical reactions that mimic the biosynthesis of natural products in nature. In a nutshell, we can learn a lot about organic synthesis from nature!
Here are a few examples of the natural products that my students and I have successfully tackled, using biomimetic strategies:
Spiculoic acid A is a polyketide isolated from the Caribbean marine sponge Plakortis angulospiculatus. It has been suggested that Spiculoic Acid A is biosynthesied through an intramolecular Diels-Alder reaction.
Xestospongins A and C are alkaloids isolated from the marine sponge Xestospongia exiguaand Araguspongine B is isolated from the Okinawan sponge Xestospongia sp. It has been postulated that these alkaloids are biosyntheised from a bis-tetrahydropyridine precursor.
Pyrinodemin A is an alkaloid isolated from the Okinawan sponge Amphimedon sp. It is believed that this natural product is biosynthesised via an intramolecular 1,3-dipolar cycloaddition reaction.
Psidial A and Guajadial are Meroterpenoids isolated from Guava leaves of Psidium guajava. These natural products are likely to be biosynthesied through a hetero-Diels-Alder reaction.
A simple and efficient version of Stille coupling was developed using readily available bench chemicals. Many research groups outside Oxford have successfully applied this methodology in natural product synthesis.
If you are interested to know more about the Part II projects, please feel free to drop me an email (email@example.com) to arrange a meeting.
- Jing He, Jack E. Baldwin, Victor Lee* Studies towards the synthesis of the antibiotic Tetrodecamycin. Synlett, 2018, 29, 1117-1121.
- Thomas W. Fenlon, Michael W. Jones, Robert M. Adlington and Victor Lee*, Synthesis of epi-Chloranthalactones A, B, D and E, Synlett, 2018, 29, 1020-1023.
- Andrew L. Lawrence, Robert M. Adlington, Jack E. Baldwin, Victor Lee*, Jessica A. Kershaw and Amber L. Thompson, A short biomimetic synthesis of the Meroterpenoids Guajadial and Psidial A, Org. Lett.,2010, 12, 1676-1679.
- James E. D. Kirkham, Victor Lee*and Jack E. Baldwin*, Biomimetic synthesis of marine sponge metabolite spiculoic acid A and establishment of the absolute configuration of the natural product, Chem. Commun., 2006, 2863-2865.
- Simon P. H. Mee, Victor Leeand Jack E. Baldwin, Significant Enhancement of the Stille Reaction with a New Combination of Reagents - Copper(I) Iodide with Cesium Fluoride, Chem. Eur. J.,2005, 11, 3294-3308.
- Simon P. H. Mee, Victor Leeand Jack E. Baldwin, Stille coupling made easier- the synergic effect of copper (I) salts and fluoride ion, Angew. Chemie Int. Ed., 2004, 43, 1132-1136.
- Jack E. Baldwin, Stuart P. Romeril, Victor Leeand Timothy C. W. Claridge, Studies towards the total synthesis of Cytotoxic Sponge Alkaloid Pyrinodemin A,Org. Lett., 2001, 1145-1148.
- Jack E. Baldwin, Artem Melman, Victor Lee, Catherine R. Firkin and Roger C. Whitehead, The Biommetic Synthesis of (+)-Araguspongine B, (-)-Xestospongin A, (+)-Xestospongin C and the Correction of their Absolute Configurations, J. Am. Chem. Soc., 1998, 120, 8559-8560.