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Synfacts 2006(5): 0416-0416  
DOI: 10.1055/s-2006-934389
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Apiosporamide

Contributor(s): Philip Kocienski, Thomas Snaddon
D. R. Williams*, D. C. Kammler, A. F. Donnell, W. R. F. Goundry
Indiana University, Bloomington, USA
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Publikationsdatum:
21. April 2006 (online)

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Significance

Isolated from Apiospora montagnei in 1994, (+)-Apiosporamide displays potent antifungal and antibacterial activity. Noteworthy in this synthesis is the use of an intramolecular Diels-­Alder cycloaddition to prepare the complete trans-decalin ring system D containing four contiguous stereocenters, controlled by a lone methyl stereocenter in enone B. This synthesis established the relative and absolute stereochemistry of the natural product.