Progress Towards the Total Synthesis of Aurantioclavine

Abstract

(–)-Aurantioclavine is an indole alkaloid isolated from the fungus Penicillium aurantiovirens that has been proposed to be a biosynthetic intermediate towards the anti-leukemic communesin alkaloids. The Doyle Lab has recently developed two reactions that are applicable to a synthesis of aurantioclavine: a three-component carbon-carbon bond-forming reductive amination, and a Ni-photoredox-catalyzed formylation of aryl chlorides. In this thesis, I discuss the merits of four main approaches towards the application of this chemistry to a synthesis of aurantioclavine. Three of these approaches were attempted experimentally, and each revealed novel aspects of reactivity within the synthetic methods themselves and the model systems at hand. Several promising leads towards an efficient synthesis of aurantioclavine using these methods were established.