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Synfacts 2006(12): 1197-1197  
DOI: 10.1055/s-2006-955593
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Guanacastepene E

Contributor(s): Philip Kocienski, Thomas Snaddon
W. D. Shipe, E. J. Sorensen*
Princeton University, USA
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

The guanacastepene diterpenes exhibit antibacterial action against drug-resistant Staphylococcus aureus and Enterococcus faecalis. Noteworthy in this synthesis are (1) fragment linkage by an accelerated π-allyl Stille reaction and (2) installation of the 5-7-fused ring system by reductive fragmentation of a cyclobutyl ketone.