The <i>N</i>-Alkylation of Agelastatin A Modulates Its Chemical Reactivity

Abstract

Agelastatin A is a marine alkaloid with potent biological activity. To date, at least 17 different strategies have achieved its total synthesis, along with many analogues. The present study focuses on the acidity stability of some N-methyl derivatives of agelastatin A. The study made use of chemical reactions and spectroscopic acquisitions. The chemical structure of some derivatives can undergo a profound rearrangement. The results could shed light on the mechanism of action of agelastatin A and suggest the preparation of analogues with improved pharmacological efficacy.

Keywords

• agelas
• agelastatin
• pyrrole-imidazole alkaloid
• <i>N</i>-acyliminium ion
• electrophilic aromatic substitution
• debromination