Journal article

Total Synthesis of (-)-histrionicotoxin 285A and (-)-perhydrohistrionicotoxin

James M Macdonald, Helen T Horsley, John H Ryan, Simon Saubern, Andrew B Holmes

ORGANIC LETTERS | AMER CHEMICAL SOC | Published : 2008

Abstract

Starting from commercially available ( S)-glycidol, and via a common intermediate, the total synthesis of (-)-histrionicotoxin 285A and (-)-perhydrohistrionicotoxin has been achieved. Key to this synthesis was the efficient construction of a six-membered, chiral, cyclic nitrone.

University of Melbourne Researchers

Grants

Funding Acknowledgements

We thank the Australian Research Council, the Commonwealth Scientific Industrial Research Organisation, the Victorian Endowment for Science Knowledge and Innovation, the Engineering and Physical Sciences Research Council, UK (Swansea National MS Service), The University of Melbourne and Merck, Sharp and Dohme (H.T.H.) for generous financial support. We thank Dr. I. Collins (industrial supervisor, MSD) and Dr. C. J. Smith (University of Cambridge) for their interest in this work.