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Synfacts 2007(2): 0119-0119  
DOI: 10.1055/s-2006-955760
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Hexacyclinol

Contributor(s): Philip Kocienski, Thomas Snaddon
J. A. Porco, Jr.*, S. Su, X. Lei, S. Bardhan, S. D. Rychnovsky
Boston University and University of California, Irvine, USA
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

(+)-Hexacyclinol is a metabolite isolated from Panus rudis strain HKI 0254 in 2002. The structure of this natural product has been the cause of recent controversy [Chem. Eng. News 2006, 84 ( 31), 11]. A synthesis of the proposed structure (J. La Clair Angew. Chem. Int. Ed. 2006, 45, 2769-2773) has recently been revised on the basis of calculated 13C NMR shifts (S. D. Rychnovsky Org. Lett. 2006, 8, 2895-2898). This work substantiates the revised structure and relates to a recent biomimetic synthesis of (+)-panepo­phenanthrin by Porco and co-workers (Angew. Chem. Int. Ed. 2003, 42, 3913-3917) that amply displays the virtues of biomimetic strategy in natural product synthesis.