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Synfacts 2007(3): 0233-0233  
DOI: 10.1055/s-2007-968198
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Chartelline C

Contributor(s): Philip Kocienski, Thomas Snaddon
P. S. Baran*, R. A. Shenvi
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

Baran and co-workers previously postulated the biosynthetic origins of the chartellines (P. S. Baran et al. Angew. Chem. Int. Ed. 2005, 44, 3714-3717), and have now disclosed a bio-inspired approach to (±)-chartelline C, the scarcest member of the group. Noteworthy in this synthesis is a remarkable four-step, one-pot cascade sequence that affords the spiro-β-lactam system characteristic of the chartellines.