Total synthesis of (±)-nicolaioidesin B via a highly regio- and diastereoselective Diels-Alder reaction

AJ Pigott; RJ Lepage; JM White; MJ Coster

Journal article

Total synthesis of (±)-nicolaioidesin B via a highly regio- and diastereoselective Diels-Alder reaction

AJ Pigott, RJ Lepage, JM White, MJ Coster

Tetrahedron Letters | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2014

DOI: 10.1016/j.tetlet.2014.10.097

Abstract

The total synthesis of (±)-nicolaioidesin B, a natural product that shows preferential cytotoxicity against pancreatic cancer cells under nutrient starvation conditions, is achieved. The key step is a thermally-induced, highly regio- and diastereoselective Diels-Alder reaction between (E)-N-methoxy-N-methylcinnamide and ocimene under solvent-free conditions.

University of Melbourne Researchers

Jonathan White Author

Related Projects (1)

Small Molecule X-ray Molecular Structure Elucidation Facility

X-ray diffraction plays a key role in identification and molecular characterisation. X-ray techniques are the single most widely used analyt..

Grants

Awarded by Australian Research Council

Funding Acknowledgements

We thank the Australian Research Council for funding (DP0956795) and a fellowship to M.J.C. We gratefully acknowledge Drs Tanja Grkovic and Hoan Vu (Griffith University) for assistance with NMR spectroscopy and mass spectrometry, respectively. We thank International Flavors and Fragrances Inc. for the generous gift of ocimene that was used in this work.