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Synfacts 2007(4): 0346-0346  
DOI: 10.1055/s-2007-968284
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Clusianone

Contributor(s): Philip Kocienski, Thomas Snaddon
V. Rodeschini, N. M. Ahmad, N. S. Simpkins*
The University of Nottingham, UK
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

Clusianone, a polyprenylated acylphloroglucinol, shows promise for cancer prevention and the treatment of HIV. This synthesis employs the Effenberger protocol (F. Effenberger and co-workers Chem. Ber. 1984, 117, 3280-3296) to access the fused bicyclic core and re­gioselective lithiation-alkylation strategies to append the remaining functionality. For a closely related synthesis of clusianone, see: P. Nuhant et al. Org. Lett. 2007, 9, 287-289.