Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids.
Organic letters – May 20, 2016
Source: PubMed
Summary
Mimicking nature's intricate chemical processes, scientists have successfully developed a "bioinspired collective synthesis" strategy. This innovative method efficiently builds multiple complex natural products, specifically seven iboga-type indole alkaloids. Using a common precursor like tabertinggine, the approach allows for the creation of diverse compounds, including ibogamine and ibogaine, through elegant biomimetic transformations. This breakthrough demonstrates a powerful new route for accessing valuable natural compounds.
Abstract
We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga-type alkaloids.