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Synfacts 2006(8): 0760-0760  
DOI: 10.1055/s-2006-941930
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Garsubellin A

Contributor(s): Philip Kocienski, Thomas Snaddon
D. R. Siegel, S. J. Danishefsky*
Sloan-Kettering Institute for Cancer Research and Columbia University, New York, USA
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

Isolated from the wood of Garcinia subelliptica, Garsubellin A enhances choline acetyltransferase activity thus providing a potential new avenue for the treatment of Alzheimer’s disease. Stereoselective preparation of the oxygenated bicyclo[3.3.1]nonane core is particularly challenging. Noteworthy in this synthesis are the preparation of D by a selective para-allylation reaction, and access to J by iodocarbocyclization.