# Bioinspired Electrochemical Cyclization toward the Divergent Synthesis of Mavacurane- and Akuammiline-Type Alkaloids

## TL;DR

A new electrochemical method enables the synthesis of two types of alkaloids from a shared precursor by adjusting redox conditions.

## Contribution

A bioinspired electrochemical approach for divergent synthesis of alkaloid frameworks using redox mediator tuning.

## Key findings

- Iodide-mediated electrolysis leads to the formation of the mavacurane core via iodination and cyclization.
- Ferrocene-mediated oxidation produces the akuammiline skeleton through radical formation.

## Abstract

We report a divergent electrochemical strategy for the
bioinspired
synthesis of mavacurane- and akuammiline-type alkaloid frameworks
from a common indole–malonate precursor. By tuning the redox
mediator, selective N–C or C–C bond formation was achieved.
Iodide-mediated electrolysis promoted iodination of the malonate carbanion,
followed by intramolecular nucleophilic cyclization to furnish the
mavacurane core. In contrast, ferrocene-mediated oxidation generated
a malonate-centered radical that afforded the akuammiline skeleton.