The application of intramolecular n-acyliminium cyclisation strategies towards biologically active heterocycles

Abstract

We describe the application of N-acyliminium cyclisation strategies to access a range of heterocycles with potential for biological activity. We have described an asymmetric approach towards the anti-tumour pyrroloisoquinoline alkaloid (R)-(+)-crispine A. We have achieved a synthesis of the pyrrolo[2,1-a]benzazepine template which is a sub-unit of the Homoerythrina alkaloids, and the functionalised dodecahydrobenz[a]indolo[3,2-h]quinolizine template, which is a sub-unit of the manadomanzamine alkaloids. In addition, we have described an asymmetric synthesis of the α-hydrazino pyrroloisoquinoline ring system, towards the synthesis of conformationally restricted peptidomimetics.