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Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole–Imidazole Alkaloids: The Total Synthesis of Ageliferin

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  • We thank Dr. D. H. Huang and Dr. L. Pasternak for NMR spectroscopic assistance, Dr. G. Siuzdak for mass spectrometric assistance, and Dr. A. Saghatelian of the Cravatt group for assistance with HPLC separations. We are grateful to Dr. M. Assmann and Dr. T. Proksch for samples of natural ageliferin, Biotage (formerly Personal Chemistry) for a generous donation of process vials used in these studies, as well as the Hertz Foundation and the Department of Defense for predoctoral Fellowships (D.P.O.). Financial support for this work was provided by The Scripps Research Institute and Eli Lilly & Co.

Abstract

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Magische Mikrowellen: Allgemein nimmt man an, dass die Biosynthese des antiviralen marinen Alkaloids Ageliferin (1) über eine Diels-Alder-Reaktion verläuft – eine experimentelle Bestätigung steht allerdings noch aus. Eine Totalsynthese von 1 ausgehend von Sceptrin führte nun zu einer alternativen Hypothese für die Biosynthese von 1 und anderen dimeren Pyrrol-Imidazol-Alkaloiden.

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