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
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.
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.