Biomimetic Synthesis of Bipleiophylline

Guillaume Vincent, Erwan Poupon and Laurent Evanno describe the biomimetic synthesis of bipleiophylline.

With over 2500 described structures, monoterpene indole alkaloids constitute a class of natural substances all derived from a single common precursor (strictosidine). These compounds are fascinating both in terms of complexity and diversity and are, needless to recall in detail, of great biological value, especially in the field of pharmacology. The synthesis of such molecules represents a challenging task for organic chemists, as well as an opportunity for developing innovative synthetic methods and strategies towards the assembling of these molecular scaffolds. Indeed, several research teams worldwide still consider monoterpene indole alkaloids as stimulating targets of choice in total synthesis. Even more challenging is the access to bis-indole alkaloids of this family. Among them, bipleiophylline, isolated from the bark of Alstonia angustifolia in Malaysia, has attracted attention since its discovery in 2008 due to its extreme complexity.

To tackle the challenge of synthesizing bipleiophylline, Dr. Guillaume Vincent’s group joined forces and knowledge with the team of Professor Erwan Poupon and Dr. Laurent Evanno within the framework of a grant from the French National Research Agency (ANR).

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