Concise synthesis of 5,8-disubstituted indolizidines and pumiliotioxins from a common intermediate

ORGN 166

Andrew D Walker, a.walker@qub.ac.uk and Paul J Stevenson, p.stevenson@qub.ac.uk. School of Chemistry, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast, BT9 5AG, United Kingdom
A wide range of biologically active alkaloids occur in the animal kingdom. The amphibians distinguish themselves as the source of a varied range of alkaloids. These alkaloids include 5,8-disubstituted indolizidines and pumiliotoxins isolated from the neotropical poison frogs of the Dendrobatidae family and the South American bufonid toads of the Melanophryniscus genus. These alkaloids possess varied and interesting pharmacology. This, combined with their scarcity from natural sources has made the 5,8-disubstituted indolizidine and pumiliotoxin alkaloids attractive targets for synthetic chemists. We have developed chemistry to synthesis the various pumiliotoxin sub-classes and the 5,8-disubstituted indolizidines from a common intermediate.