Aurantioclavine is a natural product isolated from <i>Penicillium aurantiovirens </i>that gained the interest of the synthetic community for its proposed role in the biosynthesis of the complex polycylic alkaloids of the communesin family. Members of this family display notable bioactivities, including insecticidal properties and cytotoxicity toward leukemia cell lines.<br/>Our interest in this important compound lies in its structural resemblance to tryptamine, a derivative of the amino acid tryptophan. Since tryptamine is readily available and more than a hundred times less expensive than the starting materials used in the reported total syntheses of aurantioclavine, we aim at developing a rational reaction sequence to progressively transform tryptamine and access aurantioclavine synthetically. This approach, nevertheless, is bound to involve an “unfavored” cyclization in order to assemble aurantioclavine’s characteristic seven-membered ring. We expect to tune the chemical selectivity of this process via the functionalization of the indole ring and pendant chain of tryptamine—altering the geometry and electronics of the functionalities involved in the cyclization. Our progress in these efforts will be presented.

Tuning chemoselectivity toward an affordable synthesis of aurantioclavine

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