Abstract
Pancratistatin and structurally related narciclasine are natural products of great interest as they display potent and selective activities against various diseases. A concise synthesis of a functionalised pancratistatin framework, via a Heck reaction and subsequent cyclisation, is reported. The unfunctionalised model core of pancratistatin was synthesised from 1-cyclohexene-1-carboxylic acid in two-steps in 50% yield. A modified route was then successfully applied to (−)-shikimic acid to afford a novel pancratistatin/shikimic acid hybrid analogue that possesses three stereo-defined hydroxyl groups in the C-ring.
| Original language | English |
|---|---|
| Article number | e202301247 |
| Number of pages | 7 |
| Journal | European Journal of Organic Chemistry |
| Volume | 27 |
| Issue number | 7 |
| Early online date | 18 Jan 2024 |
| DOIs | |
| Publication status | Published - 19 Feb 2024 |
Funding
The authors acknowledge the Material and Chemical Characterization Facility (MC) at the University of Bath . We wish to thank Dr Maksims Jevglevskis (University of Bath) for helpful discussions on a related project. We are grateful to the GW4 (GW4‐AF9 – 011 GW4‐BCR From Daffodils to Drugs) for financial support for MJ and DA, the University of Bath for providing a studentship for GAD and we are especially grateful to Prof. Raymond Schinazi for financial support for DA. 2 doi.org/10.15125/mx6j‐3r54
| Funders | Funder number |
|---|---|
| University of Bath |
Keywords
- Cyclization
- Heck reaction
- Natural products
- Synthetic methods
- Total synthesis
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry