Heathcock-inspired strategies for the synthesis of fawcettimine-type Lycopodium alkaloids

Abstract

The fawcettimine-type Lycopodium alkaloids have garnered significant attention from synthetic organic chemists since the isolation of fawcettimine in 1959. Despite being targets of interest for over 50 years, most of the strategies employed in the syntheses of fawcettimine congeners have built upon Inubushi and Heathcock's original work, realized in 1979 and 1986, respectively. This elegant strategy has been explored and expanded upon in the intervening years since the original publications, in what we now call the Heathcock-inspired strategy. While other disconnections have been disclosed, this strategy remains one of the most efficient. In this Concept article, we focus on exploring a number of recent Heathcock-inspired syntheses of fawcettimine-type Lycopodium alkaloids. We also briefly discuss alternative, novel disconnections.

Keywords: Heathcock-inspired strategy; Lycopodium alkaloids; fawcettimine; fused-ring systems; natural products; total synthesis.